Water → HCID 86646588, compound

Participants

Reaction Steps

Add butyl lithium (98.0 mL, 157 mmol) dropwise to a solution of diethyl methylphosphonate (23.6 g, 155 mmol) in THF (194 mL) under nitrogen at −78° C. over 15 minutes. Add (S)-3-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylic acid tert butyl ester (5.0 g, 19.4 mmol) in THF and stir at −78° C. for about 3.5 hrs. Pour into water and extract with ethyl acetate (3×). Wash the combined organics with water and brine. Dry (MgSO4), filter, and concentrate. Subject the residue to silica gel chromatography, eluting with 0-50% acetone in chloroform followed by another silica gel chromatography eluting with 0-30% acetone in dichloromethane to afford 3.15 g (47%) of the desired compound. MS (m/z)=294.0 (M−55)

Provenance & Evidence