Trifluoroacetic acid → Methyl 1-benzyl-3-(methoxymethyl)pyrrolidine-3-carboxylate

HRID 1157194Notes

Reaction equation

HRID 1157194 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[CH2:9])[C:5]([O:7][CH3:8])=[O:6].CO[CH2:12][N:13]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:14][Si](C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:8][O:7][C:5]([C:4]1([CH2:3][O:2][CH3:1])[CH2:9][CH2:12][N:13]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:14]1)=[O:6]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 10887940Methyl 2-(methoxymethyl)prop-2-enoate

Product 1

HCID 59511352Methyl 1-benzyl-3-(methoxymethyl)pyrrolidine-3-carboxylateYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 2-(methoxymethyl)acrylate (176 mg, 1.35 mmol) and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (416 μl, 1.63 mmol) in dichloromethane (2 ml) was added at 0° C. trifluoroacetic acid (21 μl, 0.27 mmol). The resulting solution was warmed to room temperature and stirred overnight. The crude product was purified by column chromatography on silica, eluted with a solution of ethyl acetate in hexanes (1:3), then 5% methanol in ethyl acetate to give the title compound (293 mg, 82%).

Workup

  1. customThe crude product was purified by column chromatography on silica
  2. washeluted with a solution of ethyl acetate in hexanes (1:3)

Sources & evidence

ORD record
ord-6d7016f635fa4b88a8ca02c8dc570116
Source dataset
uspto-grants-2010_10
Patent number
US07807672B2

Reaction notes

Loading…