Water → (r)-1-Cyclohex-3-enyl-3-[3,5-dichloro-4'-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-pyrrolidin-2-one

HRID 416020Notes

Reaction equation

HRID 416020 reaction equation
O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.[Cl:23][C:24]1[CH:25]=[C:26]([C:49]2[CH:54]=[CH:53][C:52]([C:55]([N:57]3[CH2:62][CH2:61][CH:60]([C:63]([F:66])([F:65])[F:64])[CH2:59][CH2:58]3)=[O:56])=[CH:51][CH:50]=2)[CH:27]=[C:28]([Cl:48])[C:29]=1[CH2:30][C@@H:31]1[CH2:35][CH2:34][N:33]([C@H:36]2[CH2:41][CH2:40][C@H:39](OS(C)(=O)=O)[CH2:38][CH2:37]2)[C:32]1=[O:47]>C(#N)C>[CH:36]1([N:33]2[CH2:34][CH2:35][C@@H:31]([CH2:30][C:29]3[C:24]([Cl:23])=[CH:25][C:26]([C:49]4[CH:50]=[CH:51][C:52]([C:55]([N:57]5[CH2:58][CH2:59][CH:60]([C:63]([F:66])([F:65])[F:64])[CH2:61][CH2:62]5)=[O:56])=[CH:53][CH:54]=4)=[CH:27][C:28]=3[Cl:48])[C:32]2=[O:47])[CH2:41][CH2:40][CH:39]=[CH:38][CH2:37]1

Participants

5

Reactant 3

HCID 962WaterHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 178505321HCID 178505321, compound

Product 1

HCID 57741497(r)-1-Cyclohex-3-enyl-3-[3,5-dichloro-4'-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Dissolve tetrabutylammonium fluoride trihydrate (0.436 g, 1.36 mmol) in 5 ml of acetonitrile. Add water (0.05 ml. 2.72 mmol) and stir for 10 minutes. Add trans-methanesulfonic acid 4-{(R)-3-[3,5-dichloro-4′-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-2-oxo-pyrrolidin-1-yl}-cyclohexyl ester (0.458 g, 0.68 mmol). Stir at 80° C. for 12 hours. Quench with saturated aqueous sodium bicarbonate and extract with ethyl acetate. Wash the extract with brine. Dry the organic layer over magnesium sulfate, filter, and concentrate under vacuum. Purify by silica gel chromatography recover 0.036 g (9%) of the title compound: MS (m/z): 579 (M+).

Workup

  1. customQuench with saturated aqueous sodium bicarbonate
  2. extractionextract with ethyl acetate
  3. washWash the
  4. extractionextract with brine
  5. dry with materialDry the organic layer over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify by silica gel chromatography
  9. customrecover 0.036 g (9%) of the title compound

Sources & evidence

ORD record
ord-dc2b596782074e8e8129166e1c3aa702
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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