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tarn; dihydrochloride (IVc) was dissolved in 50 cc. of methanol and hydrogenated over 6 g. of 10% pallad ized charcoal. The absorption of hydrogen was essentially complete in 90 seconds. This is a reduction rate comparable with that found with benzyl alcohol and cyclohexene and is the most rapid the senior author has observed in an iV-debenzylation except for the first step in the debenzvlation of IVb to Vb. After removal from the catalyst, the solvent was evaporated in vacuo and the residue was recrystallized from methanol.3-Acetyl-8-ethyl-3,8-diazabicyclo[3.2.1]octane (Vic). Onefiftieth mole (4.3 g.) of Vc dihydrochloride was placed in a flask and covered with 25 cc. of acetic anhydride. Three grams of potassium carbonate was added and the flask was heated, first on a steam bath, then cautiously with a free flame. There was considerable but not violent evolution of gas. As the reaction-mixture became rather thick from deposition of solid, 12 cc. more of acetic anhydride was added, and boiling was continued until the still-head, used as condenser, was thoroughly heated. Five grams more of potassium

The conversion of a A5-3/3-alcohol (I) to the corresponding A4-3-ketone (V) is an extremely important reaction in steroid chemistry and represents

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