4-oxoadamantane-1-carboxamide

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

Procedure: 26 g of 4-oxoadamantane-1-carboxamide (2) was put into a sealed container and 190 mL of 7N NH3 dissolved in MeOH was added thereto. Then, 1 g of a palladium catalyst (10 wt % Pd/C) was put into the reactor, and the reactor was filled with a nitrogen gas and the reactants were stirred for 18 hours. After the nitrogen gas was completely replaced with a hydrogen gas, the reactants were stirred for 24 hours and then filtered and distilled under a reduced pressure to provide a solid product. This solid product was placed and stirred in 100 mL of water and after the solids were removed therefrom, the remaining solution was distilled under a reduced pressure to provide 20 g of 4-aminoadamantane-1-carboxamide (3). was added the reactor was filled with a nitrogen gas the reactants were stirred for 24 hours filtered distilled under a reduced pressure to provide a solid product after the solids were removed the remaining solution was distilled under a reduced pressure

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

Procedure: 50 g of 4-oxoadamantane-1-carboxylic acid (1) was dissolved in 300 mL of MC and to the resulting solution was slowly added dropwise 30 mL of oxalic chloride. Then, five drops of DMF were added and the resulting mixture was stirred at room temperature for two hours, distilled under a reduced pressure, and then vacuum-dried. The compound as vacuum-dried was dissolved in 150 mL of anhydrous THF and the resulting solution was added dropwise to a solution prepared by mixing 60 mL of ammonia water and 150 mL of THF. This reaction was extremely exothermic and thus the reactor cooled with iced water. After being stirred for 30 minutes, solids in the reaction product were filtered off by using MC, and the organic solution being collected was dried over MgSO4 and then filtered and dried under a reduced pressure. The resulting product was recrystallized with a solution of MeOH and ether to provide 43 g of 4-oxoadamantane-1-carboxamide (2). distilled under a reduced pressure vacuum-dried The compound as vacuum-dried was dissolved in 150 mL of anhydrous THF the resulting solution was added dropwise to a solution prepared After being stirred for 30 minutes solids in the reaction product were filtered off the organic solution being collected was dried over MgSO4 filtered dried under a reduced pressure The resulting product was recrystallized with a solution of MeOH and ether

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

Procedure: More detailed explanations on Reaction Formula 1 are as follows: 4-oxoadamantane-1-carboxylic acid (1) is treated with oxalic chloride and ammonia water to prepare 4-oxoadamantane-1-carboxylic acid amide (2), and the resulting compound is treated with ammonia and subjected to a reduction reaction by using hydrogen to produce 4-aminoadamantane-1-carboxylic acid amide (3). 4-aminoadamantane-1-carboxylic acid amide thus prepared is a mixture of (E) and (Z) types, which is made into a salt form by using hydrochloric acid and then subjected to recrystallization by using acetonitrile and water to yield a pure (E) type of 4-aminoadamantane-1-carboxylic acid amide (4). subjected to a reduction reaction

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

Procedure: 26 g of 4-oxoadamantane-1-carboxamide (2) was put into a sealed container and 190 mL of 7N NH3 dissolved in MeOH was added thereto. Then, 1 g of a palladium catalyst (10 wt % Pd/C) was put into the reactor, and the reactor was filled with a nitrogen gas and the reactants were stirred for 18 hours. After the nitrogen gas was completely replaced with a hydrogen gas, the reactants were stirred for 24 hours and then filtered and distilled under a reduced pressure to provide a solid product. This solid product was placed and stirred in 100 mL of water and after the solids were removed therefrom, the remaining solution was distilled under a reduced pressure to provide 20 g of 4-aminoadamantane-1-carboxamide (3). was added the reactor was filled with a nitrogen gas the reactants were stirred for 24 hours filtered distilled under a reduced pressure to provide a solid product after the solids were removed the remaining solution was distilled under a reduced pressure

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

Procedure: 50 g of 4-oxoadamantane-1-carboxylic acid (1) was dissolved in 300 mL of MC and to the resulting solution was slowly added dropwise 30 mL of oxalic chloride. Then, five drops of DMF were added and the resulting mixture was stirred at room temperature for two hours, distilled under a reduced pressure, and then vacuum-dried. The compound as vacuum-dried was dissolved in 150 mL of anhydrous THF and the resulting solution was added dropwise to a solution prepared by mixing 60 mL of ammonia water and 150 mL of THF. This reaction was extremely exothermic and thus the reactor cooled with iced water. After being stirred for 30 minutes, solids in the reaction product were filtered off by using MC, and the organic solution being collected was dried over MgSO4 and then filtered and dried under a reduced pressure. The resulting product was recrystallized with a solution of MeOH and ether to provide 43 g of 4-oxoadamantane-1-carboxamide (2). distilled under a reduced pressure vacuum-dried The compound as vacuum-dried was dissolved in 150 mL of anhydrous THF the resulting solution was added dropwise to a solution prepared After being stirred for 30 minutes solids in the reaction product were filtered off the organic solution being collected was dried over MgSO4 filtered dried under a reduced pressure The resulting product was recrystallized with a solution of MeOH and ether

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

Procedure: More detailed explanations on Reaction Formula 1 are as follows: 4-oxoadamantane-1-carboxylic acid (1) is treated with oxalic chloride and ammonia water to prepare 4-oxoadamantane-1-carboxylic acid amide (2), and the resulting compound is treated with ammonia and subjected to a reduction reaction by using hydrogen to produce 4-aminoadamantane-1-carboxylic acid amide (3). 4-aminoadamantane-1-carboxylic acid amide thus prepared is a mixture of (E) and (Z) types, which is made into a salt form by using hydrochloric acid and then subjected to recrystallization by using acetonitrile and water to yield a pure (E) type of 4-aminoadamantane-1-carboxylic acid amide (4). subjected to a reduction reaction