Methyl iodide → 4-Methoxybenzyloxycarbonyl-(S)-isoserine methyl ester

Participants

Reaction Steps

Stir cesium carbonate (6.2 g) and N-(4-methoxybenzyloxycarbonyl-(S)-isoserine (10 g) in dimethyl formamide(DMF) (50 ml) for 1 hr. then add methyl iodide (5.4 g). Stir the resulting mixture for 18 h and concentrate in vacuo. Partition the residue between EtOAc/water and then brine. Concentrate the dried (MgSO4) EtOAc solution in vacuo to give an amber oil. Chromatograph this oil on a column of flash silica gel (1100 ml) using EtOAc:hexane (9:1) as eluant to give an amber oil, [α]D26 =+16.9° (MeOH).

Provenance & Evidence