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

HRID 1711750Notes

Reaction equation

HRID 1711750 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].[F:27][C:28]([F:41])([F:40])[C:29]1[CH:30]=[C:31](O)[CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1>>[F:27][C:28]([F:40])([F:41])[C:29]1[CH:30]=[C:31]([CH:32]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:34]=1)[O:14][CH:11]1[CH2:12][CH2:13][N:9]([C:7]([C:6]2[CH:19]=[C:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:21]=[CH:22][C:5]=2[O:4][CH:1]([CH3:3])[CH3:2])=[O:8])[CH2:10]1

Participants

3

Reactant 2

HCID 676803,5-Bis(trifluoromethyl)phenolHCID 58673069Rac-Methanesulfonic acid 1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-pyrrolidin-3-yl ester

Product 1

HCID 58673067Rac-[3-(3,5-bis-trifluoromethyl-phenoxy)-pyrrolidin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanoneYield 19%

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 3,5-bis(trifluoromethyl)phenol. The crude material was purified by reversed phase HPLC (acetonitrile/water) to yield the title compound as an amorphous white solid (yield 19%). MS (m/e): 540.3 (M+H+, 100%).

Workup

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

Sources & evidence

ORD record
ord-4805b0cc3db34e9b83ede55c51417af4
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

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