Reacción #1707692

Ecuación de reacción

sodium hydroxide

sodium triacetoxyborohydride

3-azabicyclo[3.3.1]non-7-ylmethanol hydrochloride

2,4-bis(trifluoromethyl)benzaldehyde

→

title compound

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

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was further stirred at room temperature for 30 min
2. 2
   Extracciónthe mixture was extracted with ethyl acetate
3. 3
   LavadoThe extract was washed with saturated brine
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   Otrothe solvent was evaporated under reduced pressure
6. 6
   OtroThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Procedimiento

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).

Fuente