13534-08-2Relevant articles and documents
A General Synthesis of N-Substituted 2-Azaadamantanes and Their 4,8-Disubstituted Derivatives
Henkel, James G.,Faith, William C.,Hane, Jeffrey T.
, p. 3483 - 3486 (1981)
A general synthesis of N-substituted 2-azaadamantanes (1) is reported, along with the corresponding 4,8-dihydroxy derivatives (2).The synthesis offers the advantage of the use of inexpensive and readily available starting material.Dione 3, obtained by decarboxylation of Meerwein's ester, is converted to diene 4 by Bamford-Stevens-type elimination of the corresponding ditosylhydrazone.Epoxidation of 4 affords diepoxide 12, which reacts with primary amines to form the 2-azaadamantyl skeleton 2.Removal of the hydroxyl groups to give 1 is accomplished by using SOCl2 and then LiAlH4.