Oxalyl chloride → (S)-benzyl 2-(chlorocarbonyl)-2-methylpyrrolidine-1-carboxylate

HRID 419769Notes

Reaction equation

HRID 419769 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@:12]1([CH3:19])[C:16](O)=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:23])=O>ClCCl.CN(C)C=O>[Cl:23][C:16]([C@:12]1([CH3:19])[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:17]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 18604408HCID 18604408, compound

Product 1

HCID 86643491(S)-benzyl 2-(chlorocarbonyl)-2-methylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-1-(benzyloxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid (1.50 g) in dichloromethane (30 mL) was treated with oxalyl chloride (0.65 mL) and 3 drops of N,N-dimethylformamide at ambient temperature for 1.5 hours. The mixture was concentrated and the crude material used in the next step without further purification.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe crude material used in the next step without further purification

Sources & evidence

ORD record
ord-377d50e1d6664017ba4a218ebd63499c
Source dataset
uspto-grants-2012_01
Patent number
US08093396B2

Reaction notes

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