Journal of Organic Chemistry p. 3483 - 3486 (1981)
Update date:2022-08-04
Topics:
Henkel, James G.
Faith, William C.
Hane, Jeffrey T.
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.
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