Triethylamine → 5-Oxo-alpha-hydroxy-2-pyrrolidinepropanoic acid, benzyl ester

HRID 653397Notes

Reaction equation

HRID 653397 reaction equation
[O:1]=[C:2]1[NH:6][CH:5]([CH2:7][CH:8]([OH:12])[C:9]([OH:11])=[O:10])[CH2:4][CH2:3]1.C(N(CC)CC)C.ClC(O[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=O>O1CCCC1>[O:1]=[C:2]1[NH:6][CH:5]([CH2:7][CH:8]([OH:12])[C:9]([O:11][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:10])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 201946205-Oxo-alpha-hydroxy-2-pyrrolidinepropanoic acid

Product 1

HCID 139115605-Oxo-alpha-hydroxy-2-pyrrolidinepropanoic acid, benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-oxo-alpha-hydroxy-2-pyrrolidinepropanoic acid (1.1 g), triethylamine (1.2 g), N-N-dimethylaminopyridine (1.5 g), and benzyl chloroformate (17 g) in 40 ml tetrahydrofuran is heated at reflux for 16 hours. After cooling and filtering off the triethylamine-hydrochloride, the solution was concentrated and chromatographed on SiO2 (elution with methanol:chloroform; 3:97) to yield 5-oxo-alpha-hydroxy-2-pyrrolidinepropanoic acid, benzyl ester mp 95°-96° C. NMR (CDCl3) and 7.37 (s, 5H), 7.93 (d, 1H), 5.40 (s, 1H), 1.70 (m, 2H). IR (KBr) 3330, 3200, 1733, 1691, 1497, 1456, 1389, 1351, 1287, 1216.

Workup

  1. temperatureat reflux for 16 hours
  2. temperatureAfter cooling
  3. filtrationfiltering off the triethylamine-hydrochloride
  4. concentrationthe solution was concentrated
  5. customchromatographed on SiO2 (elution with methanol:chloroform; 3:97)

Sources & evidence

ORD record
ord-125ce6a6950b438c9db44c596b40fa04
Source dataset
uspto-grants-1987_06
Patent number
US04677098

Reaction notes

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