Sodium borohydride → HCID 23138788, compound

HRID 1171695Notes

Reaction equation

HRID 1171695 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]([CH2:7][N:8]1[CH:12]=[C:11](/[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])[N:10]=[N:9]1)=[O:6]>O1CCCC1>[CH3:3][O:4][C:5]([CH2:7][N:8]1[CH:12]=[C:11](/[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])[N:10]=[N:9]1)=[O:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23139122HCID 23139122, compound

Product 1

HCID 23138788HCID 23138788, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (508 mg) was added to a solution of (E)-3-{[1-(methoxycarbonylmethyl)-1H-1,2,3-triazol-4-yl]methylidene}-1-(triphenylmethyl)piperidin-4-one (6.61 g) obtained in Example 160-(c) in tetrahydrofuran (150 ml) at 0° C. After being stirred at 0° C. for 6 hours, the mixture was filtered and the filtrate was diluted with ethyl acetate, then the reaction was quenched by addition of a saturated aqueous ammonium chloride solution. Products were extracted with ethyl acetate, and the separated organic layer was washed with a saturated aqueous sodium chloride solution. Concentration under reduced pressure gave a solid, which was collected by filtration and washed with a mixed solvent of hexane-ethyl acetate-dichloromethane (1:1:1) to afford the title compound (4.7 g, yield: 71%) as a pale yellow amorphous solid.

Workup

  1. filtrationthe mixture was filtered
  2. additionthe filtrate was diluted with ethyl acetate
  3. customthe reaction was quenched by addition of a saturated aqueous ammonium chloride solution
  4. extractionProducts were extracted with ethyl acetate
  5. washthe separated organic layer was washed with a saturated aqueous sodium chloride solution
  6. concentrationConcentration under reduced pressure
  7. customgave a solid, which
  8. filtrationwas collected by filtration
  9. washwashed with a mixed solvent of hexane-ethyl acetate-dichloromethane (1:1:1)

Sources & evidence

ORD record
ord-c4b214a8da4c4752a2df563f5d67f9ce
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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