9-cyclopropyl-9-azabicyclo[3.3.1]nonan-3-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of the above described 9-cyclopropyl-9-aza-bicyclo[3.3.1]nonan-3-one (890 mg, 5.0 mmol) in ethanol (20 mL) and hydroxylamine hydrochloride (366 mg, 5.3 mmol) was refluxed for 6 h. The reaction mixture was evaporated totally, the residue extracted with ethyl acetate and sodium bicarbonate solution, the organic layers dried over Na2SO4, filtered and the solvents evaporated to give the title compound as a white solid. (890 mg, 100%); MS: m/e=195.2 (M+H+). A mixture of the was refluxed for 6 h The reaction mixture was evaporated totally the residue extracted with ethyl acetate and sodium bicarbonate solution the organic layers dried over Na2SO4 filtered the solvents evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Glutaraldehyde (36.5 mL, 95 mmol) and 1,3-acetonedicarboxylic acid (10 g, 65 mmol) were suspended in water (100 mL) and stirred by a mechanical stirrer under argon for 30 min. To the yellow solution cyclopropylamine (3.5 mL, 50 mmol) were added in one portion whereby a slightly exothermic reaction occurred and a gas evolved. The reaction mixture was stirred at 23° C. overnight. The reaction mixture was acidified with 3 N Hydrochloride solution until pH<2, then extracted with dichloromethane. The water layer was now adjusted with 3 N NaOH to pH 8 and extracted three times with dichloromethane, the organic layers were combined, dried over MgSO4, filtered and the solvents were evaporated. Purification of the crude product by flash chromatography with n-heptane and ethyl acetate gave the title compound as a white solid (940 mg, 11%); MS: m/e=180.2 (M+H+). a slightly exothermic reaction The reaction mixture was stirred at 23° C. overnight extracted with dichloromethane extracted three times with dichloromethane dried over MgSO4 filtered the solvents were evaporated Purification of the crude product by flash chromatography with n-heptane and ethyl acetate