Hydrochloric Acid → methyl (2S,3S)-3-hydroxypyrrolidine-2-carboxylate hydrochloride

Reaction equation

[ClH:1].[OH:2][C@H:3]1[CH2:7][CH2:6][NH:5][C@@H:4]1[C:8]([OH:10])=[O:9].[CH3:11]O>>[ClH:1].[OH:2][C@H:3]1[CH2:7][CH2:6][NH:5][C@@H:4]1[C:8]([O:10][CH3:11])=[O:9]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 440575trans-3-hydroxy-L-proline

Product 1

HCID 66605223methyl (2S,3S)-3-hydroxypyrrolidine-2-carboxylate hydrochlorideYield 94%

Procedure

Hydrogen chloride gas was bubbled through a suspension of trans-3-hydroxy-L-proline (1.5 g, 11.4 mmol) in 20 ml of freshly distilled MeOH at 0° C. for 30 min. The resulting clear solution was stirred overnight, then concentrated under reduced pressure to afford the title compound as a white solid (1.96 g). Yield 94%.