4-Hydroxypyrrolidine → Rac-(3-hydroxy-pyrrolidin-1-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone

HRID 1711741Notes

Reaction equation

HRID 1711741 reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][C:6]=1[C:7]([OH:9])=O)([CH3:3])[CH3:2].[NH:18]1[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19]1>>[OH:23][CH:20]1[CH2:21][CH2:22][N:18]([C:7]([C:6]2[CH:10]=[C:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:12]=[CH:13][C:5]=2[O:4][CH:1]([CH3:2])[CH3:3])=[O:9])[CH2:19]1

Participants

3

Reactant 2

HCID 982104-HydroxypyrrolidineHCID 211002372-Isopropoxy-5-methylsulfonylbenzoic acid

Product 1

HCID 58673070Rac-(3-hydroxy-pyrrolidin-1-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanoneYield 50%

Procedure

Prepared in analogy to Example 1 from 2-isopropoxy-5-methanesulfonyl-benzoic acid (Example A1) and rac-3-pyrrolidinol. The crude material was purified by flash chromatography (methanol/dichloromethane) to yield the title compound as a light brown foam (yield 50%). MS (m/e): 328.1 (M+H+, 100%).

Workup

  1. customThe crude material was purified by flash chromatography (methanol/dichloromethane)

Sources & evidence

ORD record
ord-1cb43e291c524d658b7027ac2ea34c52
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

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