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

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).

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)

ORD record

ord-7989e75c0f5e47c8a7574d7ddecb7063

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772277B2