HCID 66687867, compound → (3,4-dichloro-phenyl)-((2R,4S)-4-fluoro-2-propyl-pyrrolidin-2-yl)-methanone

HRID 1895034Notes

Reaction equation

HRID 1895034 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([F:13])[CH2:10][C@:9]1([C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[CH2:14][CH2:15][CH3:16])=O)(C)(C)C>Cl>[Cl:25][C:20]1[CH:19]=[C:18]([C:17]([C@@:9]2([CH2:14][CH2:15][CH3:16])[CH2:10][C@H:11]([F:13])[CH2:12][NH:8]2)=[O:26])[CH:23]=[CH:22][C:21]=1[Cl:24]

Participants

3

Reactant 1

HCID 66687867HCID 66687867, compound

Product 1

HCID 66687240(3,4-dichloro-phenyl)-((2R,4S)-4-fluoro-2-propyl-pyrrolidin-2-yl)-methanoneYield 29%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (S)-2-(3,4-dichloro-benzoyl)-4-fluoro-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.220 g, 0.545 mmol) in 1N methanolic HCl (3 mL) was stirred at 20° C. under nitrogen for 18 hours. The reaction mixture was concentrated in vacuo then purified by chromatography (silica, 0 to 20% MeOH in DCM) to yield (3,4-dichloro-phenyl)-((2R,4S)-4-fluoro-2-propyl-pyrrolidin-2-yl)-methanone (0.048 g, 0.158 mmol, 29%) as a first fraction (yellow oil) then (3,4-dichloro-phenyl)-((2S,4S)-4-fluoro-2-propyl-pyrrolidin-2-yl)-methanone (0.072 g, 0.238 mmol, 44%) as a second fraction (yellow oil), each as a monohydrochloride salt, MS=304 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthen purified by chromatography (silica, 0 to 20% MeOH in DCM)

Sources & evidence

ORD record
ord-3d7106d7d68d431da87a9c3641b92362
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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