Studies on 1,2,3,4-Tetrahydroisoquinolines. VI. Reutilization of the Unwanted (R)-Isomer of (S)-(-)-5,7-Dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (TA-073)

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概要

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• Racemization of the unwanted isomer (R-1) of (S)-(-)-5,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (TA-073) via the imine 6 was examined. Reduction of 6 with NaBH_4 followed by hydrogenolysis over 10% Pd-C gave (±)-TA-073 in a good yield. Asymmetric reduction of 6 to S-4,the precursor of TA-073,by the use of the chiral reducing agent (I), prepared from NaBH_4 (1 eq) and (S)-N-benzyloxycarbonylproline (3 eq), was also investigated. Treatment of 6 with I in a halogenated alkane such as CHCl_2CH_3 or CHCl_2CHCl_2 at -30℃ afforded S-4 in an excellent optical yield (87% e.e.).

• 社団法人日本薬学会の論文
• 1983-01-25

著者

• 武田 幹男

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 大塚 久男

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 岩隈 建男

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 大塚 久男

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 岩隈 建男

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 山田 幸一郎

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 大塚 久雄

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 武田 幹男

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 武田 幹男

  田辺製薬株式会社有機化学研究所

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