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Rh(I)-Mediated rapid [11C]carboxylation using [11C]CO2 and organoborane at atmospheric pressure

Research Project

Project/Area Number 24550127
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionThe Institute of Physical and Chemical Research

Principal Investigator

DOI Hisashi  独立行政法人理化学研究所, ライフサイエンス技術基盤研究センター, チームリーダー (00421818)

Co-Investigator(Renkei-kenkyūsha) KURAI Sachi  理化学研究所ライフサイエンス技術基盤研究センター, 標識化学研究チーム, リサーチアソシエイト
GOTO Miki  理化学研究所ライフサイエンス技術基盤研究センター, 標識化学研究チーム, リサーチアソシエイト (60565779)
Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2012: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
KeywordsPET化学 / [11C]カルボキシル化 / [11C]二酸化炭素 / 常圧化学反応 / 高速化学反応 / 有機金属化学 / マイクロスケール反応器 / PET分子イメージング / PET標識化学 / 遠隔操作合成装置
Outline of Final Research Achievements

Transition-metal-mediated rapid [11C]carboxylation using organoborane and [11C]carbon dioxide ([11C]CO2) produced in a cyclotron were explored, for developing an efficient route for the 11C-labeling of carboxyl groups. After extensive experiments, we found that the use of acetone was more effective for [11C]CO2-trapping at temperatures of ca. -98 °C. As a result, [11C]carboxylation was promoted at atmospheric pressure with a short reaction time of 3-5 min using a Rh(I) catalyst. The desired [11C]benzoic acid was obtained in the decay-corrected radiochemical yield of 38%-57%.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (5 results)

All 2015 2014 2013 Other

All Presentation (3 results) (of which Invited: 2 results) Remarks (2 results)

  • [Presentation] Rh触媒による[11C]二酸化炭素を用いた[11C]カルボン酸体の高速合成2015

    • Author(s)
      後藤美樹、倉井佐知、鈴木正昭、土居久志
    • Organizer
      第10回日本分子イメージング学会
    • Place of Presentation
      タワーホール船橋(東京)
    • Year and Date
      2015-05-20 – 2015-05-21
    • Related Report
      2014 Annual Research Report
  • [Presentation] PETイメージング創薬の基盤となる標識化学技術:低分子、中分子、生体分子のPETプローブ化法2014

    • Author(s)
      土居久志
    • Organizer
      第32回メディシナルケミストリーシンポジム
    • Place of Presentation
      神戸国際会議場(神戸)
    • Year and Date
      2014-11-26 – 2014-11-28
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Application of C-11 Intermediates and Methodology: 11C-labeling methods by C-C bond formation using [11C]CH3I mediated by Pd0 catalysts2013

    • Author(s)
      Hisashi Doi
    • Organizer
      C-11 Workshop in pre-symposium in The 20th International Symposium on Radiopharmaceutical Sciences (ISRS 2013)
    • Place of Presentation
      International Convention Center (ICC) Jeju, Jeju, Korea
    • Related Report
      2013 Research-status Report
    • Invited
  • [Remarks] ライフサイエンス技術基盤研究センター・標識化学研究チームの紹介ホームページ

    • URL

      http://www.clst.riken.jp/ja/science/labs/bdi/chem/lct/

    • Related Report
      2014 Annual Research Report
  • [Remarks] 標識化学研究チーム/理化学研究所

    • URL

      http://www.riken.jp/research/labs/clst/biofunct_dyn_img/img_chem/label_chem/

    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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