Reaktion #1929003

ord-b63101582ebc440cacbc3cc7b3dae4a2

Reaktionsgleichung

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

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturwith chilling on ice
  2. 2
    Temperaturwith chilling on ice, its solvent
  3. 3
    Sonstigewas evaporated under reduced pressure
  4. 4
    workup.ADDITIONWater was added to its residue, which
  5. 5
    Extraktionwas then subjected to extraction with methylene chloride
  6. 6
    Trocknenby drying its organic layer with anhydrous magnesium sulfate
  7. 7
    SonstigeIts solvent was evaporated under reduced pressure

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE045364E1uspto-grants-2015_02