Toluene → (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

Participants

Reaction Steps

A solution of (2S,4R)-1-benzyloxycarbonyl-2-(2-oxoethyl)oxymethyl-4-methanesulfonyloxypyrrolidine (15.7 g) and ethyl 2-triphenylphosphoranylideneacetate (16.2 g) in toluene (150 ml) was heated under refluxing for 3 hours. The solvent was removed in vacuo to give a residue, which was chromatographed on silica gel (700 ml) eluting with a mixture of hexane and ethyl acetate (2:1-1:1 V/V) to give (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (12.86 g).

Provenance & Evidence