無保護アミノ酸の反応：赤堀反応 Part 2

• 横山 祐作

  東邦大学薬学部

• 椿 なつめ

  東邦大学薬学部

• 熊谷 修一

  東邦大学薬学部

• 奥野 洋明

  東邦大学薬学部

書誌事項

タイトル別名

• Reaction of Unprotected Amino Acids : Akabori Reaction Part 2

抄録

Akabori reported that the reaction of N-methylalanine (1) with benzaldehyde at 130 ^oC for 1 h in pyridine gave pseuido-ephedrine in 16% yield (Nipponkagakukaishi 1942, 64, 608-611). We have already reported on this symposium (last year) that the reaction of 1,3-benzodioxole-5-carbaldehyde (piperonal) with 1 gave the amino alcohol derivative in good yield (87% yield as a mixture of diastereomer) via unstable 3,4-dimethyl-2,5-diphenyl-oxazolidine as an intermediate. We further investigated the reaction condition of this reaction in detail. As a result, we could improve the reaction as follows: 1) The molar ratio of 1 could be decreased to 2 mol eq. from 6.5 mole eq. 2) DMSO or cyclopentyl methyl ether (CPME) could be used as a solvent. 3) The reaction temperature could be decreased to 85 ^oC from 130 ^oC. The present results are very useful information in order to develop the diastereo- and stereo-selective reactions.

収録刊行物

• 反応と合成の進歩シンポジウム 発表要旨概要

  反応と合成の進歩シンポジウム 発表要旨概要 33 (0), 13-13, 2007

  日本薬学会化学系薬学部会

キーワード

• Akabori reaction
• amino acids
• benzaldehyde
• amino alcohol
• decarboxylation

詳細情報

• CRID: 1390001205633920128
• NII論文ID: 130006996101
• DOI: 10.14895/hannou.33.0.13.0
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可