Transformations in the dibenzo[ a,d ]cycloheptene series

The synthesis of 5‐aminomethyl‐5‐hydroxy‐5 H ‐dibenzo[ a,d ]cycloheptene derivatives 3 was accomplished by two separate routes. The first route involves the reaction of 4 with Corey's Reagent followed by reaction with either amines or hydrazines. The reaction products with hydrazines ( e.g. 6 ) were hydrogenolyzed, either with hydrogen in the presence of platinum, or with hydrazine in the presence of Raney nickel to yield 3 . The second route to these compounds ( 3 ) proceeds by a Reformatsky reaction on 4 followed by acid‐hydrazide formation and Curtius degradation of 8 to afford spirooxazolidones 9 . Compounds 9 can be alkylated on nitrogen ( 10 ), and either 9 or 10 hydrolyzed to give the target compounds 3 .