Sodium borohydride → HCID 23138777, compound

HRID 1171681Notes

Reaction equation

HRID 1171681 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]([CH2:7][N:8]1[N:12]=[N:11][C:10](/[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:9]1)=[O:6]>O1CCCC1>[CH3:3][O:4][C:5]([CH2:7][N:8]1[N:12]=[N:11][C:10](/[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:9]1)=[O:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23139082HCID 23139082, compound

Product 1

HCID 23138777HCID 23138777, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (400 mg) was added to a solution of (E)-3-{[2-(methoxycarbonylmethyl)-2H-tetrazol-5-yl]methylidene}-1-(triphenylmethyl)piperidin-4-one (5.18 g) in tetrahydrofuran (100 ml) at 0° C. After the mixture was stirred at the same temperature for 2 hours, the reaction was quenched by addition of a saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate, and the extract was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The extract was concentrated under reduced pressure, and the objective material that emerged was collected by filtration. The mother liquor was concentrated and the residue was purified by silica gel chromatography using hexane, ethyl acetate, and dichloromethane (1:1:1) as an eluent to afford an additional amount of the title compound as a colourless amorphous solid. Total amount: 1.5 g, total yield: 29%.

Workup

  1. customthe reaction was quenched by addition of a saturated aqueous ammonium chloride solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe extract was concentrated under reduced pressure
  6. filtrationthe objective material that emerged was collected by filtration
  7. concentrationThe mother liquor was concentrated
  8. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-bcf0092f9c774e33b26c6f43bf2ee034
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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