Water → 3-Benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octane

HRID 645346Notes

Reaction equation

HRID 645346 reaction equation
[CH2:1]([N:8]1[C:14](=O)[CH:13]2[N:16]([CH3:17])[CH:10]([CH2:11][CH2:12]2)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>O1CCOCC1>[CH2:1]([N:8]1[CH2:14][CH:13]2[N:16]([CH3:17])[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2868213-Benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octane-2,4-dioneHCID 86616386dioxane LiAlH4

Product 1

HCID 4226713-Benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octane

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione (28.3 g, 0.116 mol) in 200 ml of absolute dioxane LiAlH4 (7.6 g, 0.2 mol) was added and the mixture boiled under argon for 18 h. Then a mixture of water (7.5 ml) and dioxane (40 ml) was added dropwise to the reaction mixture. The suspension was mixed for 20 min and filtered trough a dense glass filter. The filtrate was evaporated and the residue was distilled on Büchi oven for distillation at 120° C. and 0.1 mbar. Yield 17.6 g (70%).

Workup

  1. additionwas added dropwise to the reaction mixture
  2. additionThe suspension was mixed for 20 min
  3. filtrationfiltered trough a dense glass
  4. filtrationfilter
  5. customThe filtrate was evaporated
  6. distillationthe residue was distilled on Büchi oven for distillation at 120° C.

Sources & evidence

ORD record
ord-80da9147929747ff8873c4716c53bf3a
Source dataset
uspto-grants-2010_04
Patent number
US07704991B2

Reaction notes

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