[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]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).
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