Sodium triacetoxyborohydride → HCID 67234529, compound

HRID 75687Notes

Reaction equation

HRID 75687 reaction equation
C(O)(=O)/C=C\C(O)=O.[NH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[N:14]=[CH:13]2.[CH2:25]([N:32]1[CH2:37][CH:36]2[C:38](=O)[CH:33]1[CH2:34][CH2:35]2)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH2:25]([N:32]1[CH2:37][CH:36]2[CH:38]([NH:9][C:10]3[CH:11]=[C:12]4[C:16](=[CH:17][CH:18]=3)[N:15]([C:19](=[O:24])[C:20]([CH3:21])([CH3:23])[CH3:22])[N:14]=[CH:13]4)[CH:33]1[CH2:34][CH2:35]2)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 49759181N-Benzyl-2-azabicyclo[2.2.1]heptan-7-oneHCID 66716091HCID 66716091, compound

Product 1

HCID 67234529HCID 67234529, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(5-amino-1H-indazol-1-yl)-2,2-dimethylpropan-1-one maleate salt (580 mg, 1.7 mmol, prepared as described in U.S. Ser. No. 08/021,4614) and 2-benzyl-2-azabicyclo[2.2.1]heptan-7-one (250 mg, 1.7 mmol) (J. R. Malpass, S. Handa, and R. White, Org. Lett., 2005, 7, 2759-2762) in THF (9 mL) was added sodium triacetoxyborohydride (740 mg, 3.5 mmol), and the mixture was stirred at ambient temperature for 24 h. The reaction mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate, and the organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated and the residue was purified by normal phase chromatography followed by reversed phase HPLC to afford 175 mg (25%) of 1-(5-((1SR,4SR,7RS)-2-benzyl-2-azabicyclo[2.2.1]heptan-7-ylamino)-1H-indazol-1-yl)-2,2-dimethylpropan-1-one.

Workup

  1. customThe reaction mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by normal phase chromatography

Sources & evidence

ORD record
ord-83bc017d7f1942caafe96998ef1adcd1
Source dataset
uspto-grants-2014_09
Patent number
US08835457B2

Reaction notes

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