Ethyl Acetate → HCID 86650673, compound

HRID 1969474Notes

Reaction equation

HRID 1969474 reaction equation
[CH3:1][C:2]([NH:14][C:15]1[C:16](=[O:41])[N:17]([C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=2)[CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[CH:19]=1)([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[N:5]=1)[CH3:3].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(O)(=O)C>[CH3:3][C:2]([NH:14][CH:15]1[CH2:19][CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=2)[N:17]([C:30]2[CH:31]=[CH:32][C:33]([O:36][C:37]([F:38])([F:40])[F:39])=[CH:34][CH:35]=2)[C:16]1=[O:41])([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[N:5]=1)[CH3:1]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 86650655HCID 86650655, compound

Product 1

HCID 86650673HCID 86650673, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Dissolve (±)-3-[1-methyl-1-(6-trifluoromethyl-pyridin-2-yl)-ethylamino]-1-(4-trifluoromethoxy-phenyl)-5-(3-trifluoromethyl-phenyl)-1,5-dihydro-pyrrol-2-one (5.89 g, 10.0 mmol) in acetic acid (30 mL) and add sodium cyanoborohydride (1.26 g, 20.0 mmol). Stir for 30 min at ambient temperature. Pour reaction mixture into a mixture of saturated sodium bicarbonate solution and ethyl acetate. Extract the aqueous layer with additional ethyl acetate. Combine the organic extracts and wash with brine, dry over sodium sulfate, filter and concentrate under reduced pressure. Purify by silica gel chromatography (45% EtOAc-hexane) to yield (±)-3-[1-methyl-1-(6-trifluoromethyl-pyridin-2-yl)-ethylamino]-1-(4-trifluoromethoxy-phenyl)-5-(3-trifluoromethyl-phenyl)-pyrrolidin-2-one (2.55 g, 43%) as a racemic mixture. LC-MS ESI m/z: 592.0 (M+H)+, Tr=2.63 min., method 2

Workup

  1. additionPour
  2. customreaction mixture
  3. extractionExtract the aqueous layer with additional ethyl acetate
  4. washwash with brine
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify by silica gel chromatography (45% EtOAc-hexane)

Sources & evidence

ORD record
ord-fc8f4a1e1dba4eb690c962c6a6627434
Source dataset
uspto-grants-2013_04
Patent number
US08426448B2

Reaction notes

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