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

HRID 975641Notes

Reaction equation

HRID 975641 reaction equation
[C:1]([Cl:4])(=O)C.CO.[OH:7][C@H:8]1[CH2:12][NH:11][C@H:10]([C:13]([OH:15])=[O:14])[CH2:9]1>C(OCC)C>[ClH:4].[OH:7][C@H:8]1[CH2:12][NH:11][C@H:10]([C:13]([O:15][CH3:1])=[O:14])[CH2:9]1

Participants

5

Reactant 3

HCID 887MethanolHCID 5810L-HydroxyprolineHCID 6367Acetyl chloride

Product 1

HCID 114353194-Hydroxy-L-proline methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Acetyl chloride (380 ml) was dropwise added to methanol (3.5 l) at 10°-25° C. with stirring, followed by (2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid (500 g). The mixture was refluxed for 3 hours. The mixture was cooled to the ambient temperature and poured into diethyl ether to give precipitates. The precipitates were collected by filtration and dried up in vacuo to give methyl (2S,4R)-4-hydroxy-2-pyrrolidinecarboxylate hydrochloride (676 g).

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customto give
  3. customprecipitates
  4. filtrationThe precipitates were collected by filtration
  5. customdried up in vacuo

Sources & evidence

ORD record
ord-a8343b003c4740b793c1a0e933ee43fe
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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