A scalable synthesis of (R)-3-(2-aminopropyl)-7-benzyloxyindole via resolution

被引：17

作者：

Fujii, A

Fujima, Y

Harada, H

Ikunaka, M

Inoue, T

Kato, S

Matsuyama, K

机构：

[1] Nagase & Co Ltd, Ctr Res & Dev, Labs 1, Nishi Ku, Kobe, Hyogo 6512241, Japan

[2] Dainippon Pharmaceut Co Ltd, Drug Res Div, Chem Res Labs, Osaka 5640053, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 23期

关键词：

D O I：

10.1016/S0957-4166(02)00004-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(+/-)-3-(2-Aminopropyl)-7-benzyloxyindole 1. assembled from 7-benzyloxyindole 3 in 59% overall yield, is resolved with O.O'-di-p-toluoyl L-(2R,3R)-tartaric acid 7 into (R)-1. a key intermediate of AJ-9677 2 (selective adrenaline beta(3)-agonist) in 99.5% e.e. and 36% overall yield. The unwanted enantiomer (S)-1 (61.9% e.e.: recovered in 57% yield from the crystallization filtrate) can be reused in another round of resolution after its enantiomeric purity is lowered to 3.7% by Raney Co treatment under a hydrogen atmosphere. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3235 / 3240

页数：6

共 10 条

[1] REACTIONS OF NITRO SUGARS .27. SELECTIVE REDUCTION OF CARBOHYDRATE NITROOLEFINS [J].