Sodium Hydroxide → {3-[2,4-Bis(trifluoromethyl)benzyl]-3-azabicyclo[3.3.1]non-7-yl}methanol

HRID 1620510Notes

Reaction equation

HRID 1620510 reaction equation
Cl.[CH:2]12[CH2:12][CH:6]([CH2:7][CH:8]([CH2:10][OH:11])[CH2:9]1)[CH2:5][NH:4][CH2:3]2.[F:13][C:14]([F:28])([F:27])[C:15]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:16]=1[CH:17]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C1COCC1>[F:13][C:14]([F:27])([F:28])[C:15]1[CH:22]=[C:21]([C:23]([F:26])([F:24])[F:25])[CH:20]=[CH:19][C:16]=1[CH2:17][N:4]1[CH2:3][CH:2]2[CH2:12][CH:6]([CH2:7][CH:8]([CH2:10][OH:11])[CH2:9]2)[CH2:5]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 27360952,4-Bis(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86678702HCID 86678702, compound

Product 1

HCID 86678703{3-[2,4-Bis(trifluoromethyl)benzyl]-3-azabicyclo[3.3.1]non-7-yl}methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-azabicyclo[3.3.1]non-7-ylmethanol hydrochloride (2.54 g) in THF (66.2 mL) was added 2,4-bis(trifluoromethyl)benzaldehyde (2.82 mL). The reaction mixture was stirred at room temperature for 1 hr, and sodium triacetoxyborohydride (5.62 g) was added. The mixture was further stirred at room temperature for 30 min and poured into 0.1M aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.64 g).

Workup

  1. stirringThe mixture was further stirred at room temperature for 30 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7989e75c0f5e47c8a7574d7ddecb7063
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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