Synthesis of N,N′-di(1-adamantyl)bispidin-9-ones

Abstract

The condensation product of adamantan-1-amine with formaldehyde, 1,3,5-tri(1-adamantyl)-1,3,5-triazacyclohexane, was treated with three different types of ketones: symmetric (RCH₂)₂CO, nonsymmetric RCH₂COCH₃, and acetone to obtain 1,5-R-N,N′-di(1-adamantyl) bispidin-9-ones, N,N′-di(1-adamantyl)-1-[(1-adamantylamino)methyl]-5-methylbispidin-9-one, and N,N′-di(1-adamantyl)-1,5-bis[(1-adamantylamino)methyl]bispidin-9-one. 1,5-R-N,N′-Di(1-adamantyl)bispidin-9-ones were reduced with sodium borohydride to 1,5-R-N,N′-di(1-adamantyl)bispidin-9-ols.