1-Methyl-1H-indole-7-carboxylic acid → 1-(1-Methyl-7-indolecarbonyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(phenylhydroxymethyl)pyrrolidine

HRID 842233Notes

Reaction equation

HRID 842233 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]3[CH:19]([CH:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[OH:21])[CH2:18][NH:17][CH2:16]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:28][N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][C:36]=2[C:38](O)=[O:39])[CH:31]=[CH:30]1>>[CH3:28][N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][C:36]=2[C:38]([N:17]2[CH2:18][CH:19]([CH:20]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[OH:21])[CH:15]([CH2:14][N:11]3[CH2:12][CH2:13][CH:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:9][CH2:10]3)[CH2:16]2)=[O:39])[CH:31]=[CH:30]1

Participants

3

Reactant 2

HCID 183883621-Methyl-1H-indole-7-carboxylic acidHCID 183883753-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(RS)-(phenylhydroxymethyl)pyrrolidine

Product 1

HCID 187235011-(1-Methyl-7-indolecarbonyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(phenylhydroxymethyl)pyrrolidine

Procedure

The title compound was prepared from 3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(RS)-(phenylhydroxymethyl)pyrrolidine and 1-methyl-7-indolecarboxylic acid according to procedures described in Example 39. The crude product was purified by chromatography (silica, acetone:hexane=1:2) to give the separate diastereomers of the title compound.

Workup

  1. customThe crude product was purified by chromatography (silica, acetone:hexane=1:2)

Sources & evidence

ORD record
ord-4831431a93b2417a9f9000d4cb2e4411
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

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