2-Chloro-5-(methylsulphonyl)benzoic acid → Rac-2-(3-hydroxymethyl-pyrrolidin-1-yl)-5-methanesulfonyl-benzoic acid

HRID 32741Notes

Reaction equation

HRID 32741 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3].ClC1C=CC(S(C)(=O)=O)=CC=1[C:22](O)=[O:23].N1CCC(CO)C1>>[OH:23][CH2:22][CH:16]1[CH2:17][CH2:18][N:14]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])[CH2:15]1

Participants

4

Reactant 3

HCID 23291322-Chloro-5-(methylsulphonyl)benzoic acidHCID 13400657(Pyrrolidin-3-yl)methanolHCID 597934895-Methanesulfonyl-2-pyrrolidin-1-yl-benzoic acid

Product 1

HCID 59793550Rac-2-(3-hydroxymethyl-pyrrolidin-1-yl)-5-methanesulfonyl-benzoic acidYield 39%

Procedure

The title compound was synthesised according to the procedure described for the synthesis of 5-Methanesulfonyl-2-pyrrolidin-1-yl-benzoic acid (Example Y) from 2-Chloro-5-methanesulfonyl-benzoic acid and rac-pyrrolidin-3-yl-methanol and obtained in 39% yield. MS (m/e): 298.1 (M−H, 100%).

Workup

  1. customobtained in 39% yield

Sources & evidence

ORD record
ord-d5080999366c46b5b42605764bfd43cc
Source dataset
uspto-grants-2008_09
Patent number
US07427612B2

Reaction notes

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