Aluminium lithium hydride → [4-Aminomethyl-4-methyl-1-phenylcyclohexyl]-dimethylamine

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Reaction Steps

Lithium aluminium hydride (1.82 g, 48.0 mmol) was suspended in abs. THF (200 mL) in argon, mixed in drops with a solution of the title compound from step 3 (6.25 g, 24.0 mmol) in abs. THF (20 mL) and boiled for 4 h with reflux. The batch was then hydrolysed with water (20 mL) at 10° C. and filtered off over diatomaceous earth. The THF was removed in a vacuum, the residue adjusted to pH 11 with 1N NaOH and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4, concentrated to low volume in a vacuum and the remaining residue separated by flash chromatography with MeOH+1% NH3.

Provenance & Evidence