Reacción #1929003

ord-b63101582ebc440cacbc3cc7b3dae4a2

Ecuación de reacción

[BH4-].[Na+]
Sodium borohydride
O=C1C2CCCC1CN(Cc1ccccc1)C2
( 28 )
O=C1C2CCCC1CN(Cc1ccccc1)C2
N-benzyl-3-azabicyclo[3.3.1]nonane-9-one
OC1C2CCCC1CN(Cc1ccccc1)C2
crude compound ( 29 )
Rendimiento 191.5%
OC1C2CCCC1CN(Cc1ccccc1)C2
N-benzyl-3-azabicyclo[3.3.1]nonane-9-ol
Rendimiento 191.5%
O=C1C2CCCC1CN(Cc1ccccc1)C2
N-benzyl-3-azabicyclo[3.3.1]nonane-9-one

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturawith chilling on ice
  2. 2
    Temperaturawith chilling on ice, its solvent
  3. 3
    Otrowas evaporated under reduced pressure
  4. 4
    workup.ADDITIONWater was added to its residue, which
  5. 5
    Extracciónwas then subjected to extraction with methylene chloride
  6. 6
    Secadoby drying its organic layer with anhydrous magnesium sulfate
  7. 7
    OtroIts solvent was evaporated under reduced pressure

Procedimiento

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).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: USRE045364E1uspto-grants-2015_02