Thionyl Chloride → 1-Pyrrolidinecarboxylic acid, 2-(chlorocarbonyl)-, phenylmethyl ester

HRID 415247Notes

Reaction equation

HRID 415247 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]([OH:18])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>ClCCl>[Cl:21][C:16]([CH:12]1[CH2:13][CH2:14][CH2:15][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])=[O:18]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 232388N-(Carbobenzyloxy)-DL-proline

Product 1

HCID 98601531-Pyrrolidinecarboxylic acid, 2-(chlorocarbonyl)-, phenylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of compound 2.0 g of 1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid (1.0 g, 4.01 mmol) in anhydrous dichloromethane (10 mL) was added dropwise thionyl chloride (0.573 g, 4.81 mmol) at 0° C. After the addition, the solution was stirred at room temperature overnight. Solvent was removed in vacuum to give benzyl 2-(chlorocarbonyl)pyrrolidine-1-carboxylate.

Workup

  1. additionAfter the addition
  2. customSolvent was removed in vacuum

Sources & evidence

ORD record
ord-8c645471c97d446f86e03a2c8d941a2c
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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