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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 565552Generated: October 30, 2026

(2s)-Glycidyl indol-4-yl ether → (2S)-(+)-3-[4-(7-chloro-3-indolyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(4-indolyloxy)-2-propanol

https://huagongshe.com/reaction/565552

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(2s)-Glycidyl indol-4-yl etherHCID 10943254—
Reactant7-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 18545849—
SolventDimethyl sulfoxide methanolHCID 22036561—
Product(2S)-(+)-3-[4-(7-chloro-3-indolyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(4-indolyloxy)-2-propanolHCID 57229455—

Reaction Steps

The title compound was prepared in a fashion similar to that described in Example 193 from 7-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (0.50 g, 2.2 mmol) and (S)-(+)-4-(oxiranylmethoxy)-1H-indole (0.41 g, 2.2 mmol). The product was isolated as a white foam. Yield 370 mg (41%). mp 85-90° C. FDMS m/e=421 (M+ of free base). α[D]589=+3.62 (c=1.00, methanol/dimethylsulfoxide).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06172073B2
Source datasetuspto-grants-2001_01
ORD IDord-a867aee13ef94b3c8ea11b03eb050f45
Source noteuspto-grants-2001_01