2-Fluoro-4-nitrophenol → Rac-[3-(2-fluoro-4-nitro-phenoxy)-pyrrolidin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone

HRID 1711745Notes

Reaction equation

HRID 1711745 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.[F:23][C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:25]=1O>>[F:23][C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:25]=1[O: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

Participants

3

Reactant 2

HCID 98252-Fluoro-4-nitrophenolHCID 58673070Rac-(3-hydroxy-pyrrolidin-1-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone

Product 1

HCID 58673062Rac-[3-(2-fluoro-4-nitro-phenoxy)-pyrrolidin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanoneYield 23%

Procedure

Prepared in analogy to Example 4 from rac-(3-hydroxy-pyrrolidin-1-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone (Example 9(a)) and 2-fluoro-4-nitrophenol. The crude material was purified by reversed phase HPLC (acetonitrile/water) to yield the title compound as an amorphous white solid (yield 23%). MS (m/e): 467.4 (M+H+, 100%).

Workup

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

Sources & evidence

ORD record
ord-abe17297d911440298426bd12c14a4fc
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

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