2-(3,4-Dichloro-5-fluoro-benzoyl)-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester → HCID 58017274, compound

HRID 1895030Notes

Reaction equation

HRID 1895030 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([C:16](=[O:26])[C:17]1[CH:22]=[C:21]([F:23])[C:20]([Cl:24])=[C:19]([Cl:25])[CH:18]=1)[CH2:13][CH2:14][CH3:15])=O)(C)(C)C>Cl>[Cl:25][C:19]1[CH:18]=[C:17]([C:16]([C:9]2([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH2:12][NH:8]2)=[O:26])[CH:22]=[C:21]([F:23])[C:20]=1[Cl:24]

Participants

3

Reactant 1

HCID 666873182-(3,4-Dichloro-5-fluoro-benzoyl)-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58017274HCID 58017274, compoundYield 112.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-(3,4-dichloro-5-fluoro-benzoyl)-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.346 g, 0.856 mmol) in 1N methanolic HCl (8.6 mL) was stirred at ambient temperature under nitrogen for 15 hours. The reaction mixture was concentrated in vacuo then redissolved in DCM and re-concentrated in vacuo to remove excess HCl, furnishing (3,4-dichloro-5-fluoro-phenyl)-(2-propyl-pyrrolidin-2-yl)-methanone (0.294 g, quantitative yield) as a white powder, MS=304 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthen redissolved in DCM
  3. concentrationre-concentrated in vacuo
  4. customto remove excess HCl

Sources & evidence

ORD record
ord-43903f85173b4f90a3bb5b7634cbe930
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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