Methanesulfonyl chloride → Rac-Methanesulfonic acid 1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-pyrrolidin-3-yl ester

HRID 1711747Notes

Reaction equation

HRID 1711747 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][S:24](Cl)(=[O:26])=[O:25]>>[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][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:3]1)=[O:8])([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 58673070Rac-(3-hydroxy-pyrrolidin-1-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone

Product 1

HCID 58673069Rac-Methanesulfonic acid 1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-pyrrolidin-3-yl esterYield 99%

Procedure

Prepared in analogy to Example 3(b) from rac-(3-hydroxy-pyrrolidin-1-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone (Example 9(a)) and methanesulfonyl chloride. The crude material was purified by partitioning between dichoromethane and water to yield the title compound as a yellow oil (yield 99%). MS (m/e): 406.4 (M+H+, 100%).

Workup

  1. customThe crude material was purified
  2. customby partitioning between dichoromethane and water

Sources & evidence

ORD record
ord-852312fbf53e4f69b600cdc1b4b0ead7
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

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