Water → 1-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

HRID 2087089Notes

Reaction equation

HRID 2087089 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[OH:12][C@H:13]1[CH2:17][NH:16][C@H:15]([C:18]([OH:20])=[O:19])[CH2:14]1.C([O-])(O)=O.[Na+].O>CC(C)=O>[OH:12][C@H:13]1[CH2:17][N:16]([C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[C@H:15]([C:18]([OH:20])=[O:19])[CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 5810L-HydroxyprolineHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 3915171-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylateYield 101.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyl chloroformate (8.6 mL, 0.06 mol) was dissolved in acetone (12 mL), and this solution was added dropwise to a stirred solution of trans-4-Hydroxy-L-proline (6.56 g, 0.05 mol) in satd. NaHCO3 (160 mL) and H2O (24 mL). The resulting solution was stirred for 6 h at room temperature. The solution was washed with diethyl ether, and the organic layer was discarded. The aqueous layer was acidified with to pH 3 with 1 M HCl and extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated to afford 13.5 g (quantitative yield) of the desired product as an oil.

Workup

  1. washThe solution was washed with diethyl ether
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7331331684e9430caac3c89b0f06bf72
Source dataset
uspto-grants-2004_04
Patent number
US06727368B1

Reaction notes

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