Sodium borohydride → HCID 23159132, compound

HRID 252624Notes

Reaction equation

HRID 252624 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:17][CH:16]2[C:18](=[O:19])[CH:12]([CH2:13][CH2:14][CH2:15]2)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([N:10]1[CH2:17][CH:16]2[C:18](=[O:19])[CH:12]([CH2:13][CH2:14][CH2:15]2)[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[CH2:3]([N:10]1[CH2:17][CH:16]2[CH:18]([OH:19])[CH:12]([CH2:13][CH2:14][CH2:15]2)[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 156391233-Benzyl-3-azabicyclo[3.3.1]nonan-9-one

Product 2

HCID 156391233-Benzyl-3-azabicyclo[3.3.1]nonan-9-oneHCID 23159132HCID 23159132, compoundYield 191.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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).

Workup

  1. temperaturewith chilling on ice
  2. temperaturewith chilling on ice, its solvent
  3. customwas evaporated under reduced pressure
  4. additionWater was added to its residue, which
  5. extractionwas then subjected to extraction with methylene chloride
  6. dry with materialby drying its organic layer with anhydrous magnesium sulfate
  7. customIts solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-21d3bd65702d4e74804b07cbe1bfb293
Source dataset
uspto-grants-2011_01
Patent number
US07868178B2

Reaction notes

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