4-Nitro-3-trifluoromethylphenol → Rac-(2-isopropoxy-5-methanesulfonyl-phenyl)-[3-(4-nitro-3-trifluoromethyl-phenoxy)-pyrrolidin-1-yl]-methanone

HRID 1711753Notes

Reaction equation

HRID 1711753 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[CH:14]=[C:13]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=2[O:19][CH:20]([CH3:22])[CH3:21])=[O:8])[CH2:3]1.O[C:24]1[CH:25]=[CH:26][C:27]([N+:34]([O-:36])=[O:35])=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1>>[CH:20]([O:19][C:10]1[CH:11]=[CH:12][C:13]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:14][C:9]=1[C:7]([N:4]1[CH2:5][CH2:6][CH:2]([O:1][C:24]2[CH:25]=[CH:26][C:27]([N+:34]([O-:36])=[O:35])=[C:28]([C:30]([F:31])([F:33])[F:32])[CH:29]=2)[CH2:3]1)=[O:8])([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 69314-Nitro-3-trifluoromethylphenolHCID 58673070Rac-(3-hydroxy-pyrrolidin-1-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone

Product 1

HCID 58673080Rac-(2-isopropoxy-5-methanesulfonyl-phenyl)-[3-(4-nitro-3-trifluoromethyl-phenoxy)-pyrrolidin-1-yl]-methanoneYield 56%

Procedure

Prepared in analogy to Example 4 from rac-(3-hydroxy-pyrrolidin-1-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone (Example 9(a)) and 5-hydroxy-2-nitrobenzotrifluoride. The crude material was purified by reversed phase HPLC (acetonitrile/water) to yield the title compound as an amorphous white solid (yield 56%). MS (m/e): 517.5 (M+H+, 100%).

Workup

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

Sources & evidence

ORD record
ord-eeab7f3e88ef4528a080c17721e3e387
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

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