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

HRID 565566Notes

Reaction equation

HRID 565566 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[O:19]1[CH2:21][C@H:20]1[CH2:22][O:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:25]=1[CH:26]=[CH:27][NH:28]2>>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH:13]3[CH2:18][CH2:17][N:16]([CH2:21][C@H:20]([OH:19])[CH2:22][O:23][C:24]4[CH:32]=[CH:31][CH:30]=[C:29]5[C:25]=4[CH:26]=[CH:27][NH:28]5)[CH2:15][CH2:14]3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 212681856-nitro-3-(piperidin-4-yl)-1H-indole

Product 1

HCID 70217505(2S)-(+)-3-[4-(6-nitro-3-indolyl)piperidin-1-yl]-1-(4-indolyloxy)-2-propanol

Procedure

The title compound was prepared in a fashion similar to that described in Example 193 from 6-nitro-3-(piperidin-4-yl)-1H-indole (0.49 g, 2.0 mmol) and (S)-(+)-4-(oxiranylmethoxy)-1H-indole (0.40 g, 2.1 mmol). The product was isolated as a yellow crystalline solid. Yield 0.34 g (37%). mp 212-214° C. FDMS m/e=434 (M+ of free base).

Workup

  1. customThe product was isolated as a yellow crystalline solid

Sources & evidence

ORD record
ord-5003215a779a4350b4c876cfad3199f9
Source dataset
uspto-grants-2001_01
Patent number
US06172073B2

Reaction notes

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