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{"_buckets": {"deposit": "4773f68f-3b98-4741-b4ab-682b12aaa6e7"}, "_deposit": {"created_by": 1, "id": "72337", "owners": [1], "pid": {"revision_id": 0, "type": "depid", "value": "72337"}, "status": "published"}, "_oai": {"id": "oai:repo.qst.go.jp:00072337", "sets": ["28"]}, "author_link": ["712448", "712451", "712450", "712447", "712449"], "item_10005_date_7": {"attribute_name": "発表年月日", "attribute_value_mlt": [{"subitem_date_issued_datetime": "2017-05-16", "subitem_date_issued_type": "Issued"}]}, "item_10005_description_5": {"attribute_name": "抄録", "attribute_value_mlt": [{"subitem_description": "Introduction. [11C]Cyanide has been used as a useful intermediate for incorporation of 11C-labelled functional groups such as 11COOH, 11CONH2 and 11CH2NH2 into PET probes. [11C]Cyanide is generally prepared by heating [11C]CH4 under NH3 gas flow at more than 900°C in a column filled with platinum. The traditional method, however, requires an additional system for [11C]cyanide production. In this study, we explored a facile method to prepare [11C]cyanide without any special equipment, reagents and conditions. Hooker et al. reported that [11C]HCHO is readily prepared with Me3NO from [11C]MeI in DMF.[1] Augustine et al. reported that alkyl- and aryl-aldehydes can be efficiently converted to corresponding nitriles using NH2OH‧HCl in DMSO.[2] Based on these reports, we investigated the applicability of Augustine’s reaction to [11C]cyanide preparation from [11C]MeI which is commonly used for 11C-labelling.\nMethods. To a 50 μL of [11C]MeI solution in DMF or DMSO (30–50 MBq), a 50 μL of saturated Me3NO (\u003c2 mg) in DMSO was added. Saturated NH2OH‧HCl solution in DMSO (\u003c10 mg, 100μL) was subsequently added to the reaction mixture. To investigate the effect of HCl addition, 10 μL of 4M HCl/dioxane was added immediately or 2 min after the addition of NH2OH‧HCl. The reaction conditions are summarized in Table 1. Radiochemical yields (average of n=2) were determined by radio-HPLC analysis of the reaction solution.\nResults. In all reactions, [11C]MeI and [11C]HCHO were almost completely consumed, and [11C]H2CNOH and [11C]cyanide were observed as the major products at the end of reaction. The addition of HCl enhanced dehydration of [11C]H2CNOH to form [11C]cyanide (Entry 1, 3). The timing of HCl addition was important to obtain good yields of [11C]cyanide (Entry 3, 5). Efficient dehydration required heating at \u003e90°C (Entry 2–5). Based on these results, [11C]MeI, NH2OH‧HCl and HCl were serially mixed in a DMSO solution of Me3NO and reacted at 90°C (Entry 6, 7). Despite a report indicating that DMSO is not a suitable solvent for [11C]HCHO preparation from [11C]MeI,[1] we performed a DMF-free [11C]cyanide preparation experiment. This produced [11C]cyanide in 81% radiochemical yield after 10 min reaction time.\nConclusion. We have developed a facile method for efficient [11C]cyanide preparation using conventional lab-ware. Further optimization of reaction conditions and the application of the [11C]cyanide prepared with this method are in progress.\n\\n[1] J. M. Hooker, Matthias Schönberger, H. Schieferstein, J. S. Fowler, Angew. Chem. Int. Ed. 2008, 47, 5989–5992.\n[2] J. K. Augustine, A. Bombrun, R. N. Atta, Synlett, 2011, 15, 2223–2227. \nIntroduction. [11C]Cyanide has been used as a useful intermediate for incorporation of 11C-labelled functional groups such as 11COOH, 11CONH2 and 11CH2NH2 into PET probes. [11C]Cyanide is generally prepared by heating [11C]CH4 under NH3 gas flow at more than 900°C in a column filled with platinum. The traditional method, however, requires an additional system for [11C]cyanide production. In this study, we explored a facile method to prepare [11C]cyanide without any special equipment, reagents and conditions. Hooker et al. reported that [11C]HCHO is readily prepared with Me3NO from [11C]MeI in DMF.[1] Augustine et al. reported that alkyl- and aryl-aldehydes can be efficiently converted to corresponding nitriles using NH2OH‧HCl in DMSO.[2] Based on these reports, we investigated the applicability of Augustine’s reaction to [11C]cyanide preparation from [11C]MeI which is commonly used for 11C-labelling.\nMethods. To a 50 μL of [11C]MeI solution in DMF or DMSO (30–50 MBq), a 50 μL of saturated Me3NO (\u003c2 mg) in DMSO was added. Saturated NH2OH‧HCl solution in DMSO (\u003c10 mg, 100μL) was subsequently added to the reaction mixture. To investigate the effect of HCl addition, 10 μL of 4M HCl/dioxane was added immediately or 2 min after the addition of NH2OH‧HCl. The reaction conditions are summarized in Table 1. Radiochemical yields (average of n=2) were determined by radio-HPLC analysis of the reaction solution.\nResults. In all reactions, [11C]MeI and [11C]HCHO were almost completely consumed, and [11C]H2CNOH and [11C]cyanide were observed as the major products at the end of reaction. The addition of HCl enhanced dehydration of [11C]H2CNOH to form [11C]cyanide (Entry 1, 3). The timing of HCl addition was important to obtain good yields of [11C]cyanide (Entry 3, 5). Efficient dehydration required heating at \u003e90°C (Entry 2–5). Based on these results, [11C]MeI, NH2OH‧HCl and HCl were serially mixed in a DMSO solution of Me3NO and reacted at 90°C (Entry 6, 7). Despite a report indicating that DMSO is not a suitable solvent for [11C]HCHO preparation from [11C]MeI,[1] we performed a DMF-free [11C]cyanide preparation experiment. This produced [11C]cyanide in 81% radiochemical yield after 10 min reaction time.\nConclusion. We have developed a facile method for efficient [11C]cyanide preparation using conventional lab-ware. Further optimization of reaction conditions and the application of the [11C]cyanide prepared with this method are in progress.\n\\n[1] J. M. Hooker, Matthias Schönberger, H. Schieferstein, J. S. Fowler, Angew. Chem. Int. Ed. 2008, 47, 5989–5992.\n[2] J. K. Augustine, A. Bombrun, R. N. 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A preliminary study of facile [11C]cyanide preparation from [11C]methyl iodide
https://repo.qst.go.jp/records/72337
https://repo.qst.go.jp/records/72337b1dfe9e6-ae88-46e2-a333-f0f1ecf335a1
Item type | 会議発表用資料 / Presentation(1) | |||||
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公開日 | 2017-05-25 | |||||
タイトル | ||||||
タイトル | A preliminary study of facile [11C]cyanide preparation from [11C]methyl iodide | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_c94f | |||||
資源タイプ | conference object | |||||
アクセス権 | ||||||
アクセス権 | metadata only access | |||||
アクセス権URI | http://purl.org/coar/access_right/c_14cb | |||||
著者 |
Kikuchi, Tatsuya
× Kikuchi, Tatsuya× Zhang, Ming-Rong× D., Gee Antony× 菊池 達矢× 張 明栄 |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | Introduction. [11C]Cyanide has been used as a useful intermediate for incorporation of 11C-labelled functional groups such as 11COOH, 11CONH2 and 11CH2NH2 into PET probes. [11C]Cyanide is generally prepared by heating [11C]CH4 under NH3 gas flow at more than 900°C in a column filled with platinum. The traditional method, however, requires an additional system for [11C]cyanide production. In this study, we explored a facile method to prepare [11C]cyanide without any special equipment, reagents and conditions. Hooker et al. reported that [11C]HCHO is readily prepared with Me3NO from [11C]MeI in DMF.[1] Augustine et al. reported that alkyl- and aryl-aldehydes can be efficiently converted to corresponding nitriles using NH2OH‧HCl in DMSO.[2] Based on these reports, we investigated the applicability of Augustine’s reaction to [11C]cyanide preparation from [11C]MeI which is commonly used for 11C-labelling. Methods. To a 50 μL of [11C]MeI solution in DMF or DMSO (30–50 MBq), a 50 μL of saturated Me3NO (<2 mg) in DMSO was added. Saturated NH2OH‧HCl solution in DMSO (<10 mg, 100μL) was subsequently added to the reaction mixture. To investigate the effect of HCl addition, 10 μL of 4M HCl/dioxane was added immediately or 2 min after the addition of NH2OH‧HCl. The reaction conditions are summarized in Table 1. Radiochemical yields (average of n=2) were determined by radio-HPLC analysis of the reaction solution. Results. In all reactions, [11C]MeI and [11C]HCHO were almost completely consumed, and [11C]H2CNOH and [11C]cyanide were observed as the major products at the end of reaction. The addition of HCl enhanced dehydration of [11C]H2CNOH to form [11C]cyanide (Entry 1, 3). The timing of HCl addition was important to obtain good yields of [11C]cyanide (Entry 3, 5). Efficient dehydration required heating at >90°C (Entry 2–5). Based on these results, [11C]MeI, NH2OH‧HCl and HCl were serially mixed in a DMSO solution of Me3NO and reacted at 90°C (Entry 6, 7). Despite a report indicating that DMSO is not a suitable solvent for [11C]HCHO preparation from [11C]MeI,[1] we performed a DMF-free [11C]cyanide preparation experiment. This produced [11C]cyanide in 81% radiochemical yield after 10 min reaction time. Conclusion. We have developed a facile method for efficient [11C]cyanide preparation using conventional lab-ware. Further optimization of reaction conditions and the application of the [11C]cyanide prepared with this method are in progress. \n[1] J. M. Hooker, Matthias Schönberger, H. Schieferstein, J. S. Fowler, Angew. Chem. Int. Ed. 2008, 47, 5989–5992. [2] J. K. Augustine, A. Bombrun, R. N. Atta, Synlett, 2011, 15, 2223–2227. Introduction. [11C]Cyanide has been used as a useful intermediate for incorporation of 11C-labelled functional groups such as 11COOH, 11CONH2 and 11CH2NH2 into PET probes. [11C]Cyanide is generally prepared by heating [11C]CH4 under NH3 gas flow at more than 900°C in a column filled with platinum. The traditional method, however, requires an additional system for [11C]cyanide production. In this study, we explored a facile method to prepare [11C]cyanide without any special equipment, reagents and conditions. Hooker et al. reported that [11C]HCHO is readily prepared with Me3NO from [11C]MeI in DMF.[1] Augustine et al. reported that alkyl- and aryl-aldehydes can be efficiently converted to corresponding nitriles using NH2OH‧HCl in DMSO.[2] Based on these reports, we investigated the applicability of Augustine’s reaction to [11C]cyanide preparation from [11C]MeI which is commonly used for 11C-labelling. Methods. To a 50 μL of [11C]MeI solution in DMF or DMSO (30–50 MBq), a 50 μL of saturated Me3NO (<2 mg) in DMSO was added. Saturated NH2OH‧HCl solution in DMSO (<10 mg, 100μL) was subsequently added to the reaction mixture. To investigate the effect of HCl addition, 10 μL of 4M HCl/dioxane was added immediately or 2 min after the addition of NH2OH‧HCl. The reaction conditions are summarized in Table 1. Radiochemical yields (average of n=2) were determined by radio-HPLC analysis of the reaction solution. Results. In all reactions, [11C]MeI and [11C]HCHO were almost completely consumed, and [11C]H2CNOH and [11C]cyanide were observed as the major products at the end of reaction. The addition of HCl enhanced dehydration of [11C]H2CNOH to form [11C]cyanide (Entry 1, 3). The timing of HCl addition was important to obtain good yields of [11C]cyanide (Entry 3, 5). Efficient dehydration required heating at >90°C (Entry 2–5). Based on these results, [11C]MeI, NH2OH‧HCl and HCl were serially mixed in a DMSO solution of Me3NO and reacted at 90°C (Entry 6, 7). Despite a report indicating that DMSO is not a suitable solvent for [11C]HCHO preparation from [11C]MeI,[1] we performed a DMF-free [11C]cyanide preparation experiment. This produced [11C]cyanide in 81% radiochemical yield after 10 min reaction time. Conclusion. We have developed a facile method for efficient [11C]cyanide preparation using conventional lab-ware. Further optimization of reaction conditions and the application of the [11C]cyanide prepared with this method are in progress. \n[1] J. M. Hooker, Matthias Schönberger, H. Schieferstein, J. S. Fowler, Angew. Chem. Int. Ed. 2008, 47, 5989–5992. [2] J. K. Augustine, A. Bombrun, R. N. Atta, Synlett, 2011, 15, 2223–2227. |
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会議概要(会議名, 開催地, 会期, 主催者等) | ||||||
内容記述タイプ | Other | |||||
内容記述 | 22nd International symposium on radiopharmaceutical science | |||||
発表年月日 | ||||||
日付 | 2017-05-16 | |||||
日付タイプ | Issued |