Methanol → 4-Hydroxy-L-proline methyl ester hydrochloride

HRID 1053810Notes

Reaction equation

HRID 1053810 reaction equation
Cl.[OH:2][C@H:3]1[CH2:7][NH:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4]1.S(Cl)([Cl:13])=O.[CH3:15]O>>[ClH:13].[OH:2][C@H:3]1[CH2:7][NH:6][C@H:5]([C:8]([O:10][CH3:15])=[O:9])[CH2:4]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 11205991HCID 11205991, compound

Product 1

HCID 114353194-Hydroxy-L-proline methyl ester hydrochlorideYield 92%

Procedure

To a solution of (2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid hydrochloride (1.0 g, 7.6 mmol) in methanol (25 mL) at 0° C. was added thionyl chloride (0.83 mL, 11.4 mmol). The reaction was warmed to room temperature and heated at reflux overnight. After cooling to room temperature, the reaction mixture was concentrated to dryness to give the title compound (1.2 g, 92%) as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling to room temperature
  4. concentrationthe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-04467fc3a3054b50b0190a5624be67c7
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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