Sodium Methoxide → Trans-methyl 1-benzyl-4-(4-chlorophenyl)pyrrolidine-3-carboxylate

HRID 1880223Notes

Reaction equation

HRID 1880223 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])=[CH:12][CH:11]=2)[CH2:8][N:7]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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])=[CH:12][CH:11]=2)[CH2:8][N:7]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67530980(3S,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid methyl ester

Product 1

HCID 53485150Trans-methyl 1-benzyl-4-(4-chlorophenyl)pyrrolidine-3-carboxylateYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3S,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid methyl ester (7.0 g, 21.0 mmol) were dissolved in methanol (60 mL) and treated with NaOMe (30% in methanol, 0.9 mL, 4.50 mmol) 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 (5.9 g, 84%) as a colorless oil. ES-MS m/e: 330.8 (M+H+).

Workup

  1. customThe volatiles were removed

Sources & evidence

ORD record
ord-20a67b2d38f746dd8c15b82735b2fdda
Source dataset
uspto-grants-2012_11
Patent number
US08318759B2

Reaction notes

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