AbstractThe synthesis of 5‐aminomethyl‐5‐hydroxy‐5H‐dibenzo[a,d]cycloheptene derivatives3was accomplished by two separate routes. The first route involves the reaction of4with 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 yield3. The second route to these compounds (3) proceeds by a Reformatsky reaction on4followed by acid‐hydrazide formation and Curtius degradation of8to afford spirooxazolidones9. Compounds9can be alkylated on nitrogen (10), and either9or10hydrolyzed to give the target