Trifluoroacetic acid → Methyl 3-[1-(acetyloxy)ethyl]-1-(phenylmethyl)-3-pyrrolidinecarboxylate

Participants

Reaction Steps

Trifluoroacetic acid (0.5 g, 4.38 mmol) was added to a solution of methyl-3-acetoxy-2-methylenebutyrate (5 g, 29.03 mmol) (1) and N-Methoxymethyl-N-trimethylsilylmethylbenzylamine (6.89 g, 29.03 mmol) (2) in MeCl2 (100 ml) at 0° C., then stirred overnight at room temperature. The solvent was evaporated, and residue extracted with EtOAc (200 ml), NaHCO3 (30 ml and H2O (100 ml). The organic layer was separated, dried (MgSO4), filtered and solvent evaporated yielding an oil which chromatographed on silica gel eluting with 30% v/v (EtOAc/hexanes) yielding product (3) as colorless oil (7.53 g, 85% yield). ESMS MH, 306 (C17H23NO4)

Provenance & Evidence