Réaction #1929003

ord-b63101582ebc440cacbc3cc7b3dae4a2

Équation de réaction

[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 )
Rendement 191.5%
OC1C2CCCC1CN(Cc1ccccc1)C2
N-benzyl-3-azabicyclo[3.3.1]nonane-9-ol
Rendement 191.5%
O=C1C2CCCC1CN(Cc1ccccc1)C2
N-benzyl-3-azabicyclo[3.3.1]nonane-9-one

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurewith chilling on ice
  2. 2
    Températurewith chilling on ice, its solvent
  3. 3
    Autrewas 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
    Séchageby drying its organic layer with anhydrous magnesium sulfate
  7. 7
    AutreIts solvent was evaporated under reduced pressure

Mode opératoire

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

DOI: 10.6084/m9.figshare.5104873.v1Brevet: USRE045364E1uspto-grants-2015_02