Ammonia → 8-Benzyl-3,8-diazabicyclo[3.2.1]octane

HRID 747910Notes

Reaction equation

HRID 747910 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[C:10](=O)[NH:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].N>C1COCC1.O>[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][NH:11][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 219047238-Benzyl-3,8-diazabicyclo[3.2.1]octan-2-one

Product 1

HCID 120798988-Benzyl-3,8-diazabicyclo[3.2.1]octane

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

The product of Example 1E (2.88 g, 13.3 mmol) in 40 mL THF was added via cannula to a mixture of LiAlH4 (1.52 g, 39.9 mmol) in 40 mL THF at 0° C. After the addition was complete, the reaction mixture was allowed to warm to ambient temperature and stir for 2 h. The mixture was warmed to reflux and stirred for 1 h. The reaction was cooled to 0° C. then 1.5 mL H2O, 1.5 mL 15% NaOH and 4.5 mL H2O were added sequentially to quench the reaction. The material was filtered, the residue was washed with EtOAc, and the filtrate was concentrated under reduced pressure and carried on directly to the next reaction. MS (DCl/NH3) m/z 203 (M+H)+.

Workup

  1. additionAfter the addition
  2. temperatureThe mixture was warmed
  3. temperatureto reflux
  4. stirringstirred for 1 h
  5. temperatureThe reaction was cooled to 0° C.
  6. customto quench
  7. customthe reaction
  8. filtrationThe material was filtered
  9. washthe residue was washed with EtOAc
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customdirectly to the next reaction

Sources & evidence

ORD record
ord-88cbf3f97e11468b9a6481d374e33262
Source dataset
uspto-grants-2008_07
Patent number
US07399765B2

Reaction notes

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