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) and N-methoxymethyl-N-trimethylsilyl benzylamine (6.89 g, 29.03 mmol) in MeCl2 (50 ml) at 0° C. then stirred overnight at room temperature. The solvent was evaporated and the residue extracted with EtOAc (200 ml) and H2O (50 ml) and saturated NaHCO3 solution (50 ml). The organic layer was separated, dried over MgSO4 filtered and evaporated solvent. The residue chromatographed on silica gel eluting with (v:v) EtOAc:hexanes 3:1 yielding compound 2N as a colorless oil (7 g, 81.7%) LCMS (MH, 306) Retention time=2.08 minutes.

Provenance & Evidence