Sodium borohydride → HCID 23138533, compound

HRID 1171714Notes

Reaction equation

HRID 1171714 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[C:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][C:12](/[CH:21]=[C:22]2\[CH2:23][N:24]([C:29]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:25][CH2:26][C:27]\2=[O:28])=[N:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C(O)C>[C:3]([O:7][C:8]([N:10]1[C:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][C:12](/[CH:21]=[C:22]2\[CH2:23][N:24]([C:29]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:25][CH2:26][CH:27]\2[OH:28])=[N:11]1)=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23138748HCID 23138748, compound

Product 1

HCID 23138533HCID 23138533, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (300 mg) was added to a solution of (E)-3-{[1-(t-butoxycarbonyl)-5-(ethoxycarbonylmethyl)-1H-pyrazol-3-yl]methylidene}-1-(triphenylmethyl)piperidin-4-one (9.64 g) in ethanol (100 ml) at 0° C. After the mixture was stirred at the same temperature for 1.5 hours, the reaction was quenched by addition of a saturated aqueous ammonium chloride solution. The product was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure followed by purification of the residue by silica gel chromatography using hexane, ethyl acetate, and dichloromethane (1:1:1) as eluent gave the title compound (7.7 g, yield: 80%) as a pale yellow amorphous solid.

Workup

  1. customthe reaction was quenched by addition of a saturated aqueous ammonium chloride solution
  2. extractionThe product was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent under reduced pressure
  6. customfollowed by purification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-7bf547cdaff84ab385ba08cdd2b1ef1e
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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