Reaction #1929003

Reaction equation

Sodium borohydride

( 28 )

N-benzyl-3-azabicyclo[3.3.1]nonane-9-one

→

crude compound ( 29 )

Yield 191.5%

N-benzyl-3-azabicyclo[3.3.1]nonane-9-ol

Yield 191.5%

N-benzyl-3-azabicyclo[3.3.1]nonane-9-one

Solvents

MeOH

Conditions

Workup

1. 1
   Temperaturewith chilling on ice
2. 2
   Temperaturewith chilling on ice, its solvent
3. 3
   Otherwas evaporated under reduced pressure
4. 4
   workup.ADDITIONWater was added to its residue, which
5. 5
   Extractionwas then subjected to extraction with methylene chloride
6. 6
   Dryingby drying its organic layer with anhydrous magnesium sulfate
7. 7
   OtherIts solvent was evaporated under reduced pressure

Procedure

N-benzyl-3-azabicyclo[3.3.1]nonane-9-one (28) was synthesized according to a method described in J. Med. Chem. 1994, 37, 2831-2840. Sodium borohydride (1.49 g) was added into the MeOH (80 ml) solution of (28) (6.75 g) with chilling on ice. After its mixture was stirred for 1 hour with chilling on ice, its solvent was evaporated under reduced pressure. Water was added to its residue, which was then subjected to extraction with methylene chloride, followed by drying its organic layer with anhydrous magnesium sulfate. Its solvent was evaporated under reduced pressure to produce a crude compound (29) (6.52 g).

Source