Trifluoroacetic acid → HCID 58884968, compound

HRID 1038071Notes

Reaction equation

HRID 1038071 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C:4]([C:6]([F:9])([F:8])[F:7])=[CH2:5].O([CH2:13][N:14]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:15][Si](C)(C)C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]([C:4]1([C:6]([F:9])([F:8])[F:7])[CH2:5][CH2:13][N:14]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:15]1)=[O:10]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 2782391Methyl 2-(trifluoromethyl)acrylate

Product 1

HCID 58884968HCID 58884968, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred cold solution (0° C.) of 2-trifluoromethyl-acrylic acid methyl ester (308 mg, 2 mmol) and N-(methoxylmethyl)-N-(trimethylsilylmethyl)benzylamine (529 μl, 4.8 mmol) in dichloromethane (3 ml) was added slowly trifluoroacetic acid (31 μl). The resulting solution was allowed to stir at rt overnight and directly purified by column chromatography eluting with ethyl acetate in hexane (1:4) to provide 1-benzyl-3-trifluoromethyl-pyrrolidine-3-carboxylic acid methyl ester as oil (438 mg, 76%).

Workup

  1. customdirectly purified by column chromatography
  2. washeluting with ethyl acetate in hexane (1:4)

Sources & evidence

ORD record
ord-0416ea96d91c447dac657ae4c9f0f925
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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