3,4-Dichlorophenol → Rac-[3-(3,4-dichloro-phenoxy)-pyrrolidin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone

HRID 1711751Notes

Reaction equation

HRID 1711751 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].[Cl:27][C:28]1[CH:29]=[C:30](O)[CH:31]=[CH:32][C:33]=1[Cl:34]>>[Cl:27][C:28]1[CH:29]=[C:30]([CH:31]=[CH:32][C:33]=1[Cl:34])[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 72583,4-DichlorophenolHCID 58673069Rac-Methanesulfonic acid 1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-pyrrolidin-3-yl ester

Product 1

HCID 58673068Rac-[3-(3,4-dichloro-phenoxy)-pyrrolidin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanoneYield 32%

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 3,4-dichlorophenol. The crude material was purified by reversed phase HPLC (acetonitrile/water) to yield the title compound as an amorphous white solid (yield 32%). MS (m/e): 476.3 ({37Cl}M+H+, 10%), 474.3 ({37C,35Cl}M+H+, 80%), 472.2 ({35Cl}M+H+, 100%)

Workup

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

Sources & evidence

ORD record
ord-6da7458b7b9e49d084810d856907d295
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

Loading…