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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1599643Generated: October 25, 2026

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

https://huagongshe.com/reaction/1599643

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(2s)-Glycidyl indol-4-yl etherHCID 10943254—
Reactant6-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 11053072—
SolventDimethyl SulfoxideHCID 679—
Product(2S)-(+)-3-[4-(6-fluoro-3-indolyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(4-indolyloxy)-2-propanolHCID 57064041—

Reaction Steps

The title compound was prepared in a fashion similar to that described in Example 193 from 6-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (1.00 g, 4.63 mmol) and (S)-(+)-4-(oxiranylmethoxy)-1H-indole (0.88 g, 4.6 mmol). The resulting free base was obtained as a yellow foam. Yield 1.2 g (64%). mp 95°-100° C. FDMS m/e=405 (M+ of free base). α[D]589 =5.15 (c=1.01, dimethylsulfoxide).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05741789
Source datasetuspto-grants-1998_04
ORD IDord-d88cb39ea15947f4b4d4375e25426531
Source noteuspto-grants-1998_04