Methanol → Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

Participants

Reaction Conditions

Reaction Steps

A suspension of 65.0 g (0.50 mol) of cis-4-hydroxy-D-proline in 1500 mL of methanol was cooled to 0° C. and 110 mL (179 g, 1.5 mol) of thionyl chloride was added dropwise at 0-5° C. The mixture was then allowed to warm to room temperature overnight. The volatiles were removed under reduced pressure and the residue was triturated with diethyl ether to afford 98.73 g of crude cis-4-hydroxy-D-proline methyl ester hydrochloride as a white solid.

Provenance & Evidence