1-azabicyclo[2.2.2]octane-4-carboxamide

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

Procedure: To an ethyl acetate solution (465 ml) of p-methoxybenzyl 7β-formamido-3-iodomethyl-3-cephem-4-carboxylate (9.3 g) there was added dropwise over 1 hour under stirring while ice-cooling a mixed solution (176 ml) of methanol and ethyl acetate (1:4 v/v) containing 4-carbamoyl quinuclidine (2.94 g). After stirring for 30 minutes, the resulting precipitate was collected by filtration, followed by washing with ethyl acetate and then diisopropyl ether to obtain the desired product (12.0 g). After stirring for 30 minutes the resulting precipitate was collected by filtration by washing with ethyl acetate

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

Procedure: To an ethyl acetate solution (465 ml) of p-methoxybenzyl 7β-formamido-3-iodomethyl-3-cephem-4-carboxylate (9.3 g) there was added dropwise over 1 hour under stirring while ice-cooling a mixed solution (176 ml) of methanol and ethyl acetate (1:4 v/v) containing 4-carbamoyl quinuclidine (2.94 g). After stirring for 30 minutes, the resulting precipitate was collected by filtration, followed by washing with ethyl acetate and then diisopropyl ether to obtain the desired product (12.0 g). After stirring for 30 minutes the resulting precipitate was collected by filtration by washing with ethyl acetate

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

Procedure: To an ethyl acetate solution (465 ml) of p-methoxybenzyl 7β-formamido-3-iodomethyl-3-cephem-4-carboxylate (9.3 g) there was added dropwise over 1 hour under stirring while ice-cooling a mixed solution (176 ml) of methanol and ethyl acetate (1:4 v/v) containing 4-carbamoyl quinuclidine (2.94 g). After stirring for 30 minutes, the resulting precipitate was collected by filtration, followed by washing with ethyl acetate and then diisopropyl ether to obtain the desired product (12.0 g). After stirring for 30 minutes the resulting precipitate was collected by filtration by washing with ethyl acetate

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

Procedure: p-Methoxybenzyl 7β-phenylacetamido-3-chloromethyl-3-cephem-4-carboxylate (980 mg) was suspended in acetone (20 ml), and sodium iodide (362 mg) was added to the suspension and stirred at room temperature for 1 hour. To the resulting suspension was added 4-carbamoylquinuclidine (313 mg) under ice-cooled condition, and the mixture was stirred for 2 hours. The reaction mixture was filtered, and diethyl ether (70 ml) was added to the filtrate. The deposited solid was filtered to obtain the desired product (500 mg). cooled condition the mixture was stirred for 2 hours The reaction mixture was filtered diethyl ether (70 ml) was added to the filtrate The deposited solid was filtered

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

Procedure: t-Butyl 7β-amino-3-bromomethyl-3-cephem-4-carboxylate 1-oxide hydrobromide (600 mg) was dissolved in N,N-dimethylformamide (6 ml), and 4-carbamoylquinuclidine (456 mg) was added thereto, and the mixture was stirred in argon gas stream at room temperature for 14 hours. To the reaction solution was added diethyl ether (120 ml), the resulting precipitate was filtered and washed with n-hexane, whereby the desired product (580 mg) was obtained. the resulting precipitate was filtered washed with n-hexane, whereby the desired product (580 mg) was obtained

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

Procedure: t-Butyl 7β-amino-3-bromomethyl-3-cephem-4-carboxylate 1-oxide hydrobromide (600 mg) was dissolved in N,N-dimethylformamide (6 ml), and 4-carbamoylquinuclidine (456 mg) was added thereto, and the mixture was stirred in argon gas stream at room temperature for 14 hours. To the reaction solution was added diethyl ether (120 ml), the resulting precipitate was filtered and washed with n-hexane, whereby the desired product (580 mg) was obtained. the resulting precipitate was filtered washed with n-hexane, whereby the desired product (580 mg) was obtained

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

Procedure: To an ethyl acetate solution (465 ml) of p-methoxybenzyl 7β-formamido-3-iodomethyl-3-cephem-4-carboxylate (9.3 g) there was added dropwise over 1 hour under stirring while ice-cooling a mixed solution (176 ml) of methanol and ethyl acetate (1:4 v/v) containing 4-carbamoyl quinuclidine (2.94 g). After stirring for 30 minutes, the resulting precipitate was collected by filtration, followed by washing with ethyl acetate and then diisopropyl ether to obtain the desired product (12.0 g). After stirring for 30 minutes the resulting precipitate was collected by filtration by washing with ethyl acetate

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

Procedure: p-Methoxybenzyl 7β-phenylacetamido-3-chloromethyl-3-cephem-4-carboxylate (980 mg) was suspended in acetone (20 ml), and sodium iodide (362 mg) was added to the suspension and stirred at room temperature for 1 hour. To the resulting suspension was added 4-carbamoylquinuclidine (313 mg) under ice-cooled condition, and the mixture was stirred for 2 hours. The reaction mixture was filtered, and diethyl ether (70 ml) was added to the filtrate. The deposited solid was filtered to obtain the desired product (500 mg). cooled condition the mixture was stirred for 2 hours The reaction mixture was filtered diethyl ether (70 ml) was added to the filtrate The deposited solid was filtered

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

Procedure: t-Butyl 7β-amino-3-bromomethyl-3-cephem-4-carboxylate 1-oxide hydrobromide (600 mg) was dissolved in N,N-dimethylformamide (6 ml), and 4-carbamoylquinuclidine (456 mg) was added thereto, and the mixture was stirred in argon gas stream at room temperature for 14 hours. To the reaction solution was added diethyl ether (120 ml), the resulting precipitate was filtered and washed with n-hexane, whereby the desired product (580 mg) was obtained. the resulting precipitate was filtered washed with n-hexane, whereby the desired product (580 mg) was obtained

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

Procedure: To an ethyl acetate solution (465 ml) of p-methoxybenzyl 7β-formamido-3-iodomethyl-3-cephem-4-carboxylate (9.3 g) there was added dropwise over 1 hour under stirring while ice-cooling a mixed solution (176 ml) of methanol and ethyl acetate (1:4 v/v) containing 4-carbamoyl quinuclidine (2.94 g). After stirring for 30 minutes, the resulting precipitate was collected by filtration, followed by washing with ethyl acetate and then diisopropyl ether to obtain the desired product (12.0 g). After stirring for 30 minutes the resulting precipitate was collected by filtration by washing with ethyl acetate

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

Procedure: To an ethyl acetate solution (465 ml) of p-methoxybenzyl 7β-formamido-3-iodomethyl-3-cephem-4-carboxylate (9.3 g) there was added dropwise over 1 hour under stirring while ice-cooling a mixed solution (176 ml) of methanol and ethyl acetate (1:4 v/v) containing 4-carbamoyl quinuclidine (2.94 g). After stirring for 30 minutes, the resulting precipitate was collected by filtration, followed by washing with ethyl acetate and then diisopropyl ether to obtain the desired product (12.0 g). After stirring for 30 minutes the resulting precipitate was collected by filtration by washing with ethyl acetate

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

Procedure: p-Methoxybenzyl 7β-phenylacetamido-3-chloromethyl-3-cephem-4-carboxylate (980 mg) was suspended in acetone (20 ml), and sodium iodide (362 mg) was added to the suspension and stirred at room temperature for 1 hour. To the resulting suspension was added 4-carbamoylquinuclidine (313 mg) under ice-cooled condition, and the mixture was stirred for 2 hours. The reaction mixture was filtered, and diethyl ether (70 ml) was added to the filtrate. The deposited solid was filtered to obtain the desired product (500 mg). cooled condition the mixture was stirred for 2 hours The reaction mixture was filtered diethyl ether (70 ml) was added to the filtrate The deposited solid was filtered