Sodium cyanoborohydride → HCID 86650668, compound

HRID 1969468Notes

Reaction equation

HRID 1969468 reaction equation
[CH3:1][C:2]([NH:14][C:15]1[C:16](=[O:37])[N:17]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH:34]([F:36])[F:35])=[CH:29][CH:28]=2)[CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])[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+]>CC(O)=O>[CH3:3][C:2]([NH:14][CH:15]1[CH2:19][CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])[N:17]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH:34]([F:36])[F:35])=[CH:31][CH:32]=2)[C:16]1=[O:37])([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

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 86650654HCID 86650654, compound

Product 1

HCID 86650668HCID 86650668, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Dissolve (±)-3-[1-methyl-1-(6-trifluoromethyl-pyridin-2-yl)-ethylamino]-1-(4-difluoromethoxy-phenyl)-5-(2-fluoro-phenyl)-1,5-dihydro-pyrrol-2-one (2.06 g; 3.95 mmol) in HOAc (20 mL) and add sodium cyanoborohydride (0.50 g, 7.90 mmol). Stir for 2 hours at ambient temperature. Concentrate under reduced pressure and dissolve the residue in EtOAc. Wash the organic phase with 1N NaOH, water, saturated sodium chloride solution, dry over sodium sulfate, filter and concentrate under reduced pressure. Purify by silica gel chromatography (5-25% EtOAc-hexane) to yield (±)-3-[1-methyl-1-(6-trifluoromethyl-pyridin-2-yl)-ethylamino]-5-(2-fluoro-phenyl)-1-(4-difluoromethoxy-phenyl)-pyrrolidin-2-one (1.5 g, 73%), a racemic mixture, as a clear colorless oil. LC-MS ESI m/z: 524 (M+H)+, Tr=3.18 min., method 1.

Workup

  1. concentrationConcentrate under reduced pressure
  2. dissolutiondissolve the residue in EtOAc
  3. washWash the organic phase with 1N NaOH, water, saturated sodium chloride solution
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customPurify by silica gel chromatography (5-25% EtOAc-hexane)

Sources & evidence

ORD record
ord-0b63b2d68bef4c9c984817bb1b9d2f3b
Source dataset
uspto-grants-2013_04
Patent number
US08426448B2

Reaction notes

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