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

HRID 1605945Notes

Reaction equation

HRID 1605945 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[C:10](=O)[N:11]([CH3:17])[C:12]2=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(N1CC2N(C)C(CC2)C1)C1C=CC=CC=1>O1CCCC1>[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][N:11]([CH3:17])[CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 4226713-Benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octaneHCID 21226445Aluminium lithium hydrideHCID 215454938-Benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione

Product 1

HCID 215455078-Benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reduction of 9.6 g (0.039 mole) of 8-benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione with lithium aluminum hydride in tetrahydrofuran by the procedure used for the preparation of 3-benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octane, as described in Example 1, gave 8.3 g of crude desired product. Chromatography on 124 g alumina with chloroform elution gave 6.9 g (81%) of pure, oil 8-benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane. The hydrochloride salt, formed in diethyl ether by addition of three equivalents of ethanolic hydrogen chloride, melted at 263.5°-272° C (dec.) with sublimation above 180° C.

Workup

  1. customgave 8.3 g of crude desired product
  2. washChromatography on 124 g alumina with chloroform elution

Sources & evidence

ORD record
ord-011c34f7d7f8440ebb6f96d7e73636c4
Source dataset
uspto-grants-1976_04
Patent number
US03951980

Reaction notes

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