(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidine → (2R)-1-[(1R)-1-(2-Bromo phenyl)ethoxy]-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]propan-2-ol

HRID 1920796Notes

Reaction equation

HRID 1920796 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][CH2:11][C@H:12]1[CH2:14][O:13]1)[CH3:9].[F:15][C:16]1[CH:17]=[C:18]([CH:25]=[CH:26][C:27]=1[CH3:28])[CH2:19][C@@H:20]1[CH2:24][CH2:23][CH2:22][NH:21]1>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][CH2:11][C@H:12]([OH:13])[CH2:14][N:21]1[CH2:22][CH2:23][CH2:24][C@H:20]1[CH2:19][C:18]1[CH:25]=[CH:26][C:27]([CH3:28])=[C:16]([F:15])[CH:17]=1)[CH3:9]

Participants

3

Reactant 2

HCID 58580794(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidineHCID 58981243(2R)-2-[[(1R)-1-(2-bromophenyl)ethoxy]methyl]oxirane

Product 1

HCID 58580875(2R)-1-[(1R)-1-(2-Bromo phenyl)ethoxy]-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]propan-2-olYield 92%

Procedure

By using (2R)-2-{[(1R)-1-(2-bromo phenyl)ethoxy]methyl}oxirane described in WO 2004/106280 and (2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidine which had been obtained in Example 1 (1e), the reaction was carried out in the same manner as the method described in Example 1 (1f) to give the title compound as a colorless oily substance (yield 92%).

Sources & evidence

ORD record
ord-c7fbe9c4d76947ceace951b9857279f1
Source dataset
uspto-grants-2012_05
Patent number
US08173631B2

Reaction notes

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