Diethyl Ether → (4R)-4-Hydroxy-L-proline methyl ester

HRID 1199737Notes

Reaction equation

HRID 1199737 reaction equation
[C:1](Cl)(=O)C.[OH:5][C@H:6]1[CH2:10][NH:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7]1.CCOCC>CO>[CH3:1][O:12][C:11]([C@@H:8]1[CH2:7][C@@H:6]([OH:5])[CH2:10][NH:9]1)=[O:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 5810L-HydroxyprolineHCID 6367Acetyl chloride2×

Product 1

HCID 7015125(4R)-4-Hydroxy-L-proline methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Acetyl chloride (7.6 ml; 107 mmol) was added slowly to MeOH (70 ml). The reaction was exothermic. (2S,4R)-4-Hydroxy-2-pyrrolidinecarboxylic acid (10 g; 76.2 mmol) was added and the mixture was refluxed for 4 hours. At this time, another portion of 3 ml of acetyl chloride in 30 ml of MeOH was added. The mixture was refluxed an additional 3 hours. The reaction was cooled to room temperature and ~750 ml of Et2O was added. The resulting colorless crystals were filtered and dried to afford 11.89 g of the title A compound.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. temperatureThe mixture was refluxed an additional 3 hours
  3. filtrationThe resulting colorless crystals were filtered
  4. customdried
  5. customto afford 11.89 g of the title A compound

Sources & evidence

ORD record
ord-f35c5d4173f244faab5b16afa4df6ebd
Source dataset
uspto-grants-1990_02
Patent number
US04902684

Reaction notes

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