Sodium borohydride → HCID 178467818, compound

HRID 2368161Notes

Reaction equation

HRID 2368161 reaction equation
[BH4-].[Na+].[CH:3]1([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]3[C:15]([CH:16]=2)=[N:14][N:13]([C@H:17]2[CH2:22][CH2:21][C@H:20]([CH2:23][CH2:24][C:25](=[O:27])[CH3:26])[CH2:19][CH2:18]2)[CH:12]=3)[CH2:5][CH2:4]1>C(O)C>[CH:3]1([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]3[C:15]([CH:16]=2)=[N:14][N:13]([C@H:17]2[CH2:22][CH2:21][C@H:20]([CH2:23][CH2:24][CH:25]([OH:27])[CH3:26])[CH2:19][CH2:18]2)[CH:12]=3)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178467817HCID 178467817, compound

Product 1

HCID 178467818HCID 178467818, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.306 g) was added to a solution of 4-{trans-4-[6-(cyclopropylmethoxy)-2H-indazol-2-yl]cyclohexyl}butan-2-one (2.75 g) in ethanol (100 mL) under ice-cooling in small portions. The reaction mixture was stirred at room temperature for 1 hr, and the mixture was concentrated under reduced pressure. The residue was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (2.46 g).

Workup

  1. temperaturecooling in small portions
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d6450282d39e4623b9e8b8f4d30d8c4e
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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