1-(3,5-Difluoro-4-hydroxyphenyl)propan-1-one → Rac-1-{3,5-difluoro-4-[1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-pyrrolidin-3-yloxy]-phenyl}-propan-1-one

HRID 1711742Notes

Reaction equation

HRID 1711742 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.[CH3:23][CH2:24][C:25]([C:27]1[CH:32]=[C:31]([F:33])[C:30](O)=[C:29]([F:35])[CH:28]=1)=[O:26]>>[F:33][C:31]1[CH:32]=[C:27]([C:25](=[O:26])[CH2:24][CH3:23])[CH:28]=[C:29]([F:35])[C:30]=1[O:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7](=[O:8])[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])[CH2:3]1

Participants

3

Reactant 2

HCID 5194791-(3,5-Difluoro-4-hydroxyphenyl)propan-1-oneHCID 58673070Rac-(3-hydroxy-pyrrolidin-1-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone

Product 1

HCID 58673066Rac-1-{3,5-difluoro-4-[1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-pyrrolidin-3-yloxy]-phenyl}-propan-1-oneYield 21%

Procedure

Prepared in analogy to Example 4 from rac-(3-hydroxy-pyrrolidin-1-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone and 3,5-difluoro-4-hydroxypropiophenone. The crude material was purified by reversed phase HPLC (acetonitrile/water) to yield the title compound as an amorphous white solid (yield 21%). MS (m/e): 496.5 (M+H+, 100%).

Workup

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

Sources & evidence

ORD record
ord-de61c5a94b6a493d86a856df7c925c0d
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

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