(r)-2-[(4s,5s)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hex-(z)-ylidene-pyrrolidine-1-carboxylic acid tert-butyl ester → (r)-2-[(4s,5s)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hexyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

Combine (R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hex-(Z)-ylidene-pyrrolidine-1-carboxylic acid tert-butyl ester (0.04 g, 0.076 mmol), 10% palladium on carbon (4 mg) and methanol (2 mL) and stir for 2 days under 1 atmosphere of hydrogen. Add filter agent, filter and concentrate under reduced pressure to provide the desired compound as a mixture of isomers (2:1 4(S):4(R); 0.036 g, 90%). Subject isomer mixture to HPLC chromatography under acidic conditions: TFA 0.05% at pH 2.5; Organic solvent: acetonitrile; Gradient from 90 to 95% acetonitrile.

Provenance & Evidence