2-Butyl-2-(3,4-dichloro-benzoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester → (2-Butyl-pyrrolidin-2-yl)-(3,4-dichloro-phenyl)-methanone

HRID 661541Notes

Reaction equation

HRID 661541 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:23][CH2:24][CH2:25][CH3:26])[C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)=O)(C)(C)C>Cl.CO>[CH2:23]([C:9]1([C:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)=[O:22])[CH2:10][CH2:11][CH2:12][NH:8]1)[CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 1

HCID 666879182-Butyl-2-(3,4-dichloro-benzoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58017261(2-Butyl-pyrrolidin-2-yl)-(3,4-dichloro-phenyl)-methanoneYield 68%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 2-butyl-2-(3,4-dichloro-benzoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.435 g, 1.09 mmol) in 1N HCl in MeOH (10.9 mL) was stirred at ambient temperature under nitrogen for 14 hours. The reaction mixture was concentrated in vacuo, then redissolved in DCM and concentrated in vacuo to remove excess HCl. Purification by chromatography (silica, 0-10% MeOH in DCM) gave (2-butyl-pyrrolidin-2-yl)-(3,4-dichloro-phenyl)-methanone (0.249 g, 0.740 mmol, 68%) as a white powder, MS=300 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionredissolved in DCM
  3. concentrationconcentrated in vacuo
  4. customto remove excess HCl
  5. customPurification by chromatography (silica, 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-ae9598a046e047d7a3ebeeccd62db64f
Source dataset
uspto-grants-2011_12
Patent number
US08084623B2

Reaction notes

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