HCID 20271667, compound → 2-Methyl-2-azabicyclo[2.2.2]octan-5-amine

HRID 484641Notes

Reaction equation

HRID 484641 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]([CH:10]1[CH2:15][CH:14]2[CH2:16][CH2:17][CH:11]1[CH2:12][N:13]2[C:18](OCC)=O)=[N+]=[N-]>C1COCC1>[NH2:7][CH:10]1[CH2:15][CH:14]2[CH2:16][CH2:17][CH:11]1[CH2:12][N:13]2[CH3:18]

Participants

4

Reactant 2

HCID 20271667HCID 20271667, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 147882832-Methyl-2-azabicyclo[2.2.2]octan-5-amineYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of LiAlH4 (2 g) in dry THF (100 was added a solution of the (±)-5-azido-2-carbethoxy-2-azabicyclo[2,2,2]octane (D3a) (3.5 g) under dry nitrogen and the mixture heated under reflux for 5 hrs. Normal basic work-up afforded the crude (±) 5-amino-2-methyl-2-azabicyclo[2,2,2]octane (D4a) (1.6 g, 70%), purified by distillation (b.p. 75°/5 mmHg).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 5 hrs

Sources & evidence

ORD record
ord-5236e8ba9cbc42c982d7a7ac9eb47974
Source dataset
uspto-grants-1985_08
Patent number
US04533498

Reaction notes

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