(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide → 1-[(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-one

HRID 906927Notes

Reaction equation

HRID 906927 reaction equation
CON(C)[C:4]([CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH2:9][N:8]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:7]1)=[O:5].[CH2:27]([Li])[CH3:28]>C1COCC1>[CH2:19]([N:8]1[CH2:9][CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH:6]([C:4](=[O:5])[CH2:27][CH3:28])[CH2:7]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 86627620(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amideHCID 178506846HCID 178506846, compound

Product 1

HCID 671316011-[(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-oneYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide (described herein above) 377 mg (0.959 mmol) dissolved in THF (4 mL) was added 0.676 mL (1.15 mmol) of ethyllithium (1.7M in dibutylether) dropwise at −78° C. and stirred for one hour. The reaction was quenched by aq. ammonium chloride solution and extracted with ethylacetate. The separated organic layer was dired on anhydrous sodium sulfate and concentrated in vaccuo. The residue was purified by silica gel column chromatography eluted by a mixture of heptane and ethyl acetate (10:1) yielding 212 mg (61%) of the title compound as a light yellow oil. ES-MS m/e: 362.2 (M+H+).

Workup

  1. customThe reaction was quenched by aq. ammonium chloride solution
  2. extractionextracted with ethylacetate
  3. concentrationconcentrated in vaccuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluted by a mixture of heptane and ethyl acetate (10:1)

Sources & evidence

ORD record
ord-2f03cbb8fe8f46d8aaee08b6b7a506d2
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

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