Methanol → methyl (2S)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

HRID 496245Notes

Reaction equation

HRID 496245 reaction equation
[OH:1][CH:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.S(Cl)([Cl:12])=O.[CH3:14]O>>[ClH:12].[OH:1][CH:2]1[CH2:6][NH:5][C@H:4]([C:7]([O:9][CH3:14])=[O:8])[CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 69248L-Proline, 4-hydroxy-, cis-

Product 1

HCID 12764091methyl (2S)-4-hydroxypyrrolidine-2-carboxylate hydrochlorideYield 97%

Procedure

To a solution of 33.0 g (0.25 mol) of 4-hydroxy-(L)-proline and 200 mL of MeOH was added 20 mL (0.27 mol) of thionyl chloride. The reaction was warmed to reflux for 16 h and then cooled to rt and concentrated in vacuo. Trituration with Et2O afforded 44 g (97%) of 4-hydroxy-(L)-proline, methyl ester hydrochloride as a white solid which was used without further purification.

Workup

  1. temperatureThe reaction was warmed
  2. temperatureto reflux for 16 h
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-621ec1b092694250a7b7f48d6006c0d9
Source dataset
uspto-grants-2005_09
Patent number
US06943180B2

Reaction notes

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