Sodium triacetoxyborohydride → HCID 67234529, compound

HRID 445121Notes

Reaction equation

HRID 445121 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-9ecff77c26a84fdf8b2db14e0c8b1d2c
Source dataset
uspto-grants-2013_07
Patent number
US08476295B2

Reaction notes

Loading…