Thionyl Chloride → Ethyl 3-(chlorocarbonyl)pyrrolidine-1-carboxylate

HRID 981610Notes

Reaction equation

HRID 981610 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][CH:8]([C:11]([OH:13])=O)[CH2:7]1)=[O:5])[CH3:2].S(Cl)([Cl:16])=O>ClCCl>[Cl:16][C:11]([CH:8]1[CH2:9][CH2:10][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7]1)=[O:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14989183HCID 14989183, compound

Product 1

HCID 14989184Ethyl 3-(chlorocarbonyl)pyrrolidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 44 parts of 1-(ethoxycarbonyl)-3-pyrrolidinecarboxylic acid in 520 parts of dichloromethane were added dropwise 35.7 parts of thionyl chloride at 20° C. Upon complete addition, stirring was continued overnight and the reaction mixture was evaporated, yielding 49 parts (100%) of ethyl 3-(chlorocarbonyl)-1-pyrrolidinecarboxylate as an oily residue (int. 25).

Workup

  1. additionUpon complete addition
  2. customthe reaction mixture was evaporated

Sources & evidence

ORD record
ord-785b818c212d404b9dd8881538f3b4ca
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

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