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

HRID 661554Notes

Reaction equation

HRID 661554 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-a065371728f3461392ccac46a1d252b6
Source dataset
uspto-grants-2011_12
Patent number
US08084623B2

Reaction notes

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