9-Amino-3-(amino or nitro)-1,5-dioxaspiro{8 5.5{9 undecane derivatives

Abstract

Abstract 9-(Ac1NH)-3-Q-3-R-9-R''-1,5-dioxaspiro(5.5)undecane (I), where R and R'' are each hydrogen or lower-alkyl, Ac1 is hydrogen or lower-alkanoyl and Q is NO2 or NH2, are useful intermediates for the preparation of antifertility agents, namely, 3-(Ac4NH)-9(Ac3NH)-3-R-9-R''-1,5-dioxaspiro(5.5)undecane (II), where Ac3 is lower-alkanoyl or 4-Q1-benzoyl, Ac is 4-Q2-benzoyl, Q1 and Q2 are each lower-alkoxy or polyhalo-lower-alkoxy, and, R and R'' are each hydrogen or lower-alkyl. II is prepared by diacylating I where Ac1 is hydrogen and Q is NH2 (VII) or by monoacylating I where Ac1 is lower-alkanoyl and Q is NH2 (VI). VI and VII are prepared stepwise as follows: 4-(Ac5NH)-4-R''-cyclohexanol (X), where Ac5 is lower-alkanoyl, is oxidized to produce 4-(Ac5NH)-4R''-cyclohexanone (III); III is reacted with 2-NO2-R-1,3propanediol (IV) to produce 9-(Ac5NH)-3-nitro-3-R-9-R''-1,5dioxaspiro(5.5)undecane (V); V is reduced to produce 3-amino-9(Ac5NH)-3-R-9-R''-1,5-dioxaspiro(5.5)undecane (VI); and, VI is hydrolyzed to produce 3-R-9-R''-1,5-dioxaspiro(5.5)undecan-3,9diamine (VII). Methods of preparing X are given. Bis(polyhaloacetyl) derivatives of VII are prepared.

Inventors

• 👤 Karl O Gelotte
• 👤 Alexander R Surrey

Bibliographic Details