Cyclohexanone → HCID 19040168, compound

Participants

Reaction Steps

To a solution of 8-t-butyl-3-aminomethyl-3-hydroxy-1-oxaspiro-(4,5)decane (1.8 g, 7.5 mmol), cyclohexanone (1.36 g, 8 mmol) and zinc chloride (0.61 g, 4.5 mmol) in methanol (20 ml) was added sodium cyanoborohydride (0.56 g, 9 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was then evaporated in vacuo and to the resulting residue was added saturated sodium carbonate solution and toluene (50 ml each). The organic layer was separated, dried (MgSO4) and evaporated in vacuo to yield a semisolid residue (2.0 g) which was treated with light petroleum. A colourless powder was isolated by filtration (1.0 g) which melted at 113°-115° C.

Provenance & Evidence