Oxalyl chloride → 1-Pyrrolidinecarboxylic acid, 2-(chlorocarbonyl)-, phenylmethyl ester

HRID 1170469Notes

Reaction equation

HRID 1170469 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[C:7]([N:17]1C[CH2:23][CH2:22][CH:18]1C(O)=O)([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]>CN(C)C=O.C(Cl)Cl>[CH2:10]([O:9][C:7]([N:17]1[CH2:18][CH2:22][CH2:23][CH:1]1[C:2]([Cl:4])=[O:3])=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 232388N-(Carbobenzyloxy)-DL-proline

Product 1

HCID 98601531-Pyrrolidinecarboxylic acid, 2-(chlorocarbonyl)-, phenylmethyl esterYield 98.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (1.21 mL, 14.0 mmol) was added dropwise (15 minutes) to a 0° C. solution of N-carbobenzyloxy-D,L-proline (2.50 g, 10.0 mmol), dimethylformamide (1 drop, cat.) and methylene chloride (anhydrous, 25 mL) under a nitrogen atmosphere. The mixture was removed from the ice-bath and stirred at ambient temperature for 1 h. The reaction mixture was concentrated to afford 2.63 g (98%) of 2-chlorocarbonyl-pyrrolidine-1-carboxylic acid benzyl ester as an orange oil. The product was used directly in subsequent steps.

Workup

  1. customThe mixture was removed from the ice-bath
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-ee80f50a05894dc1b70da2b169f0a568
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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