Sodium Methoxide → methyl (3R*,4S*)-1-benzyl-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate

HRID 1880226Notes

Reaction equation

HRID 1880226 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:8][N:7]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6]1)=[O:4].C[O-].[Na+]>CO>[CH3:1][O:2][C:3]([C@@H:5]1[C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:8][N:7]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67131510(3S,4S)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methyl ester

Product 1

HCID 67232866methyl (3R*,4S*)-1-benzyl-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylateYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3S,4S)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methyl ester (37.5 g, 0.107 mol) were dissolved in methanol (300 mL) and treated with NaOMe (30% in methanol, 2.97 mL, 0.016 mol) for 24 h at ambient temperature. The volatiles were removed and the residue was subjected to column chromatography (silica gel, heptane/ethyl acetate 9:1) to yield the title compound (32.0 g, 82%) as a colorless oil. ES-MS m/e: 365.3 (M+H+).

Workup

  1. customThe volatiles were removed

Sources & evidence

ORD record
ord-d9679995e6904b89af8ae10942a9ee2b
Source dataset
uspto-grants-2012_11
Patent number
US08318759B2

Reaction notes

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