3-(Trifluoromethyl)phenol → Rac-(2-isopropoxy-5-methanesulfonyl-phenyl)-[3-(3-trifluoromethyl-phenoxy)-pyrrolidin-1-yl]-methanone

HRID 1711749Notes

Reaction equation

HRID 1711749 reaction equation
[CH:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][C:6]=1[C:7]([N:9]1[CH2:13][CH2:12][CH:11]([O:14]S(C)(=O)=O)[CH2:10]1)=[O:8])([CH3:3])[CH3:2].O[C:28]1[CH:29]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:32][CH:33]=1>>[CH:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][C:6]=1[C:7]([N:9]1[CH2:13][CH2:12][CH:11]([O:14][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[CH2:10]1)=[O:8])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 73763-(Trifluoromethyl)phenolHCID 58673069Rac-Methanesulfonic acid 1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-pyrrolidin-3-yl ester

Product 1

HCID 58673071Rac-(2-isopropoxy-5-methanesulfonyl-phenyl)-[3-(3-trifluoromethyl-phenoxy)-pyrrolidin-1-yl]-methanoneYield 45%

Procedure

Prepared in analogy to Example 3(c) from rac-methanesulfonic acid 1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-pyrrolidin-3-yl ester (Example 14(a)) and 3-hydroxybenzotrifluoride. The crude material was purified by reversed phase HPLC (acetonitrile/water) to yield the title compound as an amorphous white solid (yield 45%). MS (m/e): 472.4 (M+H+, 100%).

Workup

  1. customThe crude material was purified by reversed phase HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-0054dcbbf9d44f72b00f6a79298f98d2
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

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