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

HRID 1268991Notes

Reaction equation

HRID 1268991 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].[CH3:11][O:9][C:8]([C@@H:4]1[C@@H:3]([OH:2])[CH2:7][CH2:6][NH:5]1)=[O:10]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 440575trans-3-hydroxy-L-proline

Product 1

HCID 66605223methyl (2S,3S)-3-hydroxypyrrolidine-2-carboxylate hydrochlorideYield 93.7%

Procedure

Part A. Hydrogen chloride gas was bubbled into a stirred suspension of trans-3-hydroxy-L-proline (25 g, 190 mmol) in MeOH (250 mL) at 0° C. for 10 min. The resulting clear solution was capped and stirred at room temperature for 6 h. It was concentrated under reduced pressure. The resulting white solids were triturated with either, filtered, and dried under vacuum to give (2S,3S)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride salt (32.5 g, yield: 93.7%).

Workup

  1. customThe resulting clear solution was capped
  2. concentrationIt was concentrated under reduced pressure
  3. customThe resulting white solids were triturated with either,
  4. filtrationfiltered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-8a81ce16aaa140158d0bd21bb33e4c23
Source dataset
uspto-grants-2007_04
Patent number
US07199149B2

Reaction notes

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