Benzyl Bromide → (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carboxylic acid

HRID 1264404Notes

Reaction equation

HRID 1264404 reaction equation
[CH3:1][S:2]([N:5]1[CH2:9][C@H:8]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:7][C@H:6]1[C:20]([OH:22])=[O:21])(=[O:4])=[O:3].[Li+].CC([N-]C(C)C)C.[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.OS([O-])(=O)=O.[K+].CCOC(C)=O>C1COCC1>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][S:10][C@H:8]2[CH2:9][N:5]([S:2]([CH2:1][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:3])=[O:4])[C@H:6]([C:20]([OH:22])=[O:21])[CH2:7]2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 2724682Lithium diisopropylamideHCID 70002772(2S,4R)-1-Methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-2-carboxylic acidHCID 86585043ethylacetate KHSO4

Product 1

HCID 70002412(2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carboxylic acidYield 138.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 138 mg (0.4 mmol) (2S,4R)-1-Methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-2-carboxylic acid in 8 ml THF was treated at −78° C. with 0.83 ml (1.24 mmol, 1.5 M THF solution) of LDA. After 30 min 0.17 ml (1.4 mmol) benzylbromide were added and warmed up to RT over night. The reaction was poured into aqueous 10% KHSO4/EtOAc (3×). The organic phases were washed with aqueous 10% NaCl solution and dried over Na2SO4 to give 242 mg (quantitativ) crude (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carboxylic acid.

Workup

  1. washThe organic phases were washed with aqueous 10% NaCl solution
  2. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-df47024dc6a740e7bb002ab979d48f8a
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

Loading…