Sodium borohydride → HCID 23138890, compound

HRID 1171690Notes

Reaction equation

HRID 1171690 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]([CH2:7][N:8]1[C:12](/[CH:13]=[C:14]2\[CH2:15][N:16]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:18][C:19]\2=[O:20])=[CH:11][N:10]=[N:9]1)=[O:6]>O1CCCC1>[CH3:3][O:4][C:5]([CH2:7][N:8]1[C:12](/[CH:13]=[C:14]2\[CH2:15][N:16]([C:21]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:17][CH2:18][CH:19]\2[OH:20])=[CH:11][N:10]=[N:9]1)=[O:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23138477HCID 23138477, compound

Product 1

HCID 23138890HCID 23138890, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (830 mg) was added to a solution of (E)-3-{[1-(methoxycarbonylmethyl)-1H-1,2,3-triazol-5-yl]methylidene}-1-(triphenylmethyl)piperidin-4-one (21.46 g) in tetrahydrofuran (500 ml) at 0° C. After the mixture was stirred at 0° C. for 4 hours, it was filtered, and the filtrate was diluted with ethyl acetate. Then the reaction was quenched by addition of a saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate, and the separated organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The extract was concentrated under reduced pressure and the residue was purified by silica gel chromatography using hexane, ethyl acetate, and dichloromethane (1:2:1) as an eluent to afford the title compound (6.27 g, yield: 29%) as a pale yellow amorphous solid.

Workup

  1. filtrationit was filtered
  2. additionthe filtrate was diluted with ethyl acetate
  3. customThen the reaction was quenched by addition of a saturated aqueous ammonium chloride solution
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe separated organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe extract was concentrated under reduced pressure
  8. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-14c9b39bef1e49cc98fe006fba72f676
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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