Water → (S)-2-(Allylamino)-2-phenyl-1-(pyrrolidin-1-YL)ethanone

HRID 23575Notes

Reaction equation

HRID 23575 reaction equation
[CH2:1]([N:4]([C@@H:17]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:18](=[O:24])[N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1.O>CN(C)C=O>[CH2:1]([NH:4][C@@H:17]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:18]([N:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1)=[O:24])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 69731465N-Allyl-2-nitro-N-(2-oxo-1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide

Product 1

HCID 69730433(S)-2-(Allylamino)-2-phenyl-1-(pyrrolidin-1-YL)ethanoneYield 84.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-allyl-2-nitro-N-(2-oxo-1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide (66.2 g, 154 mmol) in anhydrous dimethylformamide (300 cm3) was added potassium carbonate (63.9 g, 462 mmol). The mixture was stirred at ambient temperature for 10 minutes and thiophenol (22.2 cm3, 216 mmol) was added dropwise over 10 minutes. The mixture was stirred for 16 hours at ambient temperature and poured into water (2000 cm3) and extracted with ethyl acetate (3×500 cm3). The combined ethyl acetate extracts were washed with water (2×400 cm3), brine (1×300 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a foul smelling yellow oil. The crude product was purified by column chromatography (silica, eluting with hexane-ethyl acetate 1:1 to 0:1 and then dichloromethane-methanol 19:1 to 9:1) to afford the title compound as a yellow viscous oil (31.9 g, 84.9%) with a positive ion ESI (M+H)+245.3.

Workup

  1. stirringThe mixture was stirred for 16 hours at ambient temperature
  2. extractionextracted with ethyl acetate (3×500 cm3)
  3. washThe combined ethyl acetate extracts were washed with water (2×400 cm3), brine (1×300 cm3)
  4. dry with materialdried over sodium sulfate, vacuum
  5. filtrationfiltered
  6. customthe volatile fractions removed in vacuo to a foul smelling yellow oil
  7. customThe crude product was purified by column chromatography (silica
  8. washeluting with hexane-ethyl acetate 1:1 to 0:1

Sources & evidence

ORD record
ord-0b6a91ccaecf4e2ba3d0e9f239536c0b
Source dataset
uspto-grants-2005_02
Patent number
US06852713B2

Reaction notes

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