A novel synthesis of a key intermediate for diltiazem

被引：41

作者：

Seki, M

Furutani, T

Imashiro, R

Kuroda, T

Yamanaka, T

Harada, N

Arakawa, H

Kusama, M

Hashiyama, T

机构：

[1] Tanabe Seiyaku Co Ltd, Prod & Technol Dev Lab, Yodogawa Ku, Osaka 5328505, Japan

[2] Tanabe Seiyaku Co Ltd, Med Chem Res Lab, Toda, Saitama 3358505, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 46期

关键词：

asymmetric synthesise; epoxidation; epoxides; catalysts; crystallization;

D O I：

10.1016/S0040-4039(01)01762-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical synthesis of methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (-)-2a, a key intermediate for diltiazem (3), was described. Treatment of methyl (E)-4-methoxycinnaniate (E)-1a with chiral dioxirane, generated in situ from a catalytic amount of an 11-membered C-2-symmetric binaplithyl ketone 7a. provided (-)-2a in 78% ee and 89% yield. The crude mixture of (-)-2a and 7a was efficiently separated by the use of novel equipment performing continuous dissolution and crystallization to furnish the optically pure (-)-2a (>99% ee) and recovery of 7a in 64 and 88% yields, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

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收藏

页码：8201 / 8205

页数：5

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