tricyclo[5.2.1.02,6]decan-8-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 2.2 g of 1,3a,4,6,7,7a-hexahydro-4,7-methanoinden-5-one oxime were dissolved in 50 ml of methanol, and about 10% Raney nickel, dissolved in 50% water, was added. The mixture was hydrogenated at 100 bar and 100° C. for 20 hours, the catalyst was then filtered off, and the solvent was evaporated under reduced pressure. The residue was taken up in ether and 6 N aqueous sodium hydroxide solution, the phases were separated, the aqueous phase was extracted three times with ether, the combined organic phases were dried with magnesium sulfate and filtered, and the filtrate was concentrated. This gave 1.8 g of a colorless oil which was purified by kugelrohr distillation. This gave 0.96 g of the desired amine as an oil. was added the catalyst was then filtered off the solvent was evaporated under reduced pressure 6 N aqueous sodium hydroxide solution, the phases were separated the aqueous phase was extracted three times with ether the combined organic phases were dried with magnesium sulfate filtered the filtrate was concentrated This gave 1.8 g of a colorless oil which was purified by kugelrohr distillation

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

Procedure: 2.2 g of 1,3a,4,6,7,7a-hexahydro-4,7-methanoinden-5-one oxime were dissolved in 50 ml of methanol, and about 10% Raney nickel, dissolved in 50% water, was added. The mixture was hydrogenated at 100 bar and 100° C. for 20 hours, the catalyst was then filtered off, and the solvent was evaporated under reduced pressure. The residue was taken up in ether and 6 N aqueous sodium hydroxide solution, the phases were separated, the aqueous phase was extracted three times with ether, the combined organic phases were dried with magnesium sulfate and filtered, and the filtrate was concentrated. This gave 1.8 g of a colorless oil which was purified by kugelrohr distillation. This gave 0.96 g of the desired amine as an oil. was added the catalyst was then filtered off the solvent was evaporated under reduced pressure 6 N aqueous sodium hydroxide solution, the phases were separated the aqueous phase was extracted three times with ether the combined organic phases were dried with magnesium sulfate filtered the filtrate was concentrated This gave 1.8 g of a colorless oil which was purified by kugelrohr distillation

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

Procedure: A solution of 15 g of tricyclo[5,2,1,02,6]decan-8-one in 60 ml of methanol, which had been saturated beforehand at 10° C. with NH3, was, after addition of Raney nickel, hydrogenated in an autoclave at 90° C. and a hydrogen pressure of 100 bar for 10 hours. The catalyst was filtered off and the solvent was distilled off under reduced pressure, and the mixture was then made strongly alkaline using 10 N NaOH and extracted 2-3 times with ethyl acetate or with diisopropyl ether. The combined organic phases were dried and subjected to fractional distillation under reduced pressure. Bp6-7mm 86-88° C. hydrogenated in an autoclave at 90° C. The catalyst was filtered off the solvent was distilled off under reduced pressure extracted 2-3 times with ethyl acetate The combined organic phases were dried subjected to fractional distillation under reduced pressure Bp6-7mm 86-88° C.

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

Procedure: 3.3 g of a mixture of 3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-5-ylamine and 3a,4,5,6,7,7a-hexahydro-3H-4,7-methanoinden-5-ylamine (example Amine 1, a2) were dissolved in 30 ml of methanol and reduced under an atmosphere of hydrogen in the presence of 0.5 g Pd/C (10%). After 4 hours the catalyst was filtered off and washed with methanol. The filtrate was concentrated in vaccuo to give 3 g of the desired product as an oil. After 4 hours the catalyst was filtered off washed with methanol The filtrate was concentrated in vaccuo

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

Procedure: 3.3 g of a mixture of 3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-5-ylamine and 3a,4,5,6,7,7a-hexahydro-3H-4,7-methanoinden-5-ylamine (example Amine 1, a2) were dissolved in 30 ml of methanol and reduced under an atmosphere of hydrogen in the presence of 0.5 g Pd/C (10%). After 4 hours the catalyst was filtered off and washed with methanol. The filtrate was concentrated in vaccuo to give 3 g of the desired product as an oil. After 4 hours the catalyst was filtered off washed with methanol The filtrate was concentrated in vaccuo

Conditions: temp:0.00; pressure:0.00; stir: