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 1895017Notes

Reaction equation

HRID 1895017 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-cb487ae0498b4ad8935cfa1dd1442aca
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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