Methanol → (2R,4S)-methyl 4-hydroxypyrrolidine-2-carboxylate

HRID 732356Notes

Reaction equation

HRID 732356 reaction equation
S(Cl)(Cl)=O.[OH:5][C@@H:6]1[CH2:10][NH:9][C@@H:8]([C:11]([OH:13])=[O:12])[CH2:7]1.[CH3:14]O>>[CH3:14][O:12][C:11]([C@H:8]1[CH2:7][C@H:6]([OH:5])[CH2:10][NH:9]1)=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 440074(2R,4S)-4-hydroxypyrrolidine-2-carboxylic acid

Product 1

HCID 7021430(2R,4S)-methyl 4-hydroxypyrrolidine-2-carboxylateYield 99%

Procedure

Add thionyl chloride (5.8 mL, 79.4 mmol) to an ice-cold suspension of 4-(S)-hydroxypyrrolidine-2-(R)-carboxylic acid (4.97 g, 31.9 mmol) in methanol (70 mL). Stir 10 min, then warm to room temperature and stir 3.5 h. Concentrate, add methanol and concentrate again to give the title compound as a white solid (7.18 g, 99%).

Workup

  1. stirringstir 3.5 h
  2. concentrationConcentrate
  3. additionadd methanol
  4. concentrationconcentrate again

Sources & evidence

ORD record
ord-e17db6fa8dcd4a458cdff2d55940ae00
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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