Sodium Hydroxide → Endo-3,9-dimethyl-3,9-diazabicyclo[3.3.1)nonan-7-ol

HRID 1656912Notes

Reaction equation

HRID 1656912 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]=[C:8]1[CH2:15][CH:14]2[N:16]([CH3:17])[CH:10]([CH2:11][N:12]([CH3:18])[CH2:13]2)[CH2:9]1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1.O>[CH3:18][N:12]1[CH2:11][CH:10]2[N:16]([CH3:17])[CH:14]([CH2:15][CH:8]([OH:7])[CH2:9]2)[CH2:13]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 197864093,9-Dimethyl-3,9-diazabicyclo[3.3.1]nonan-7-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 19786410Endo-3,9-dimethyl-3,9-diazabicyclo[3.3.1)nonan-7-olYield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (0.95 g, 25.0 mmol) in dry THF (40 ml) was added dropwise at room temperature while stirring a solution of 7-oxo-3,9-dimethyl3,9-diazabicyclo[3.3.1)nonane (2.78 g, 16.5 mmol) in dry THF (50 ml). After stirring at room temperature for 4.5 hrs, water (1 ml), 40% aqueous sodium hydroxide solution (1 ml) and water (3 ml) were added successively to a reaction solution. Further anhydrous magnesium sulfate was added and stirred, and thereafter the reaction was filtered. The filtrate was concentrated under reduced pressure to afford the title compound (2.62 g) as an oily product.

Workup

  1. additionwas added dropwise at room temperature
  2. stirringstirred
  3. filtrationthe reaction was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a16bbbad821e42aca73bc72d77918aa5
Source dataset
uspto-grants-1993_10
Patent number
US05256656

Reaction notes

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