2-METHYLQUINUCLIDIN-3-ONE

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 10.1 g (58.4 mmol) of 2-methylene-1-azabicyclo[2.2.2]octan-3-one hydrochloride hydrate, 8.1 g of K2CO3 and 100 mg of PtO2 in 100 mL of MeOH was hydrogenated at 10–15 psi H2 for about 1 hr. The solution was filtered through dicalite and the solvent was evaporated in vacuo. The residue was dissolved in CHCl3 and again filtered through dicalite. The filtrate was evaporated in vacuo to give 4.7 g (58% yield) of 2-methyl-1-azabicyclo[2.2.2]octan-3-one Compound 8A as a yellow oil. 1H NMR (CDCl3) 1.3 (d, 3H), 2.0 (m, 4H), 2.4 (t, 1H), 2.9 (m, 1H), 3.05 (, 1H), 3.2 (m, 3H). This material was used without further purification in the next step. The solution was filtered through dicalite the solvent was evaporated in vacuo The residue was dissolved in CHCl3 again filtered through dicalite The filtrate was evaporated in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-Methylenequinuclidin-3-one (17.8 g, 0.13 mol, 1 eq) is dissolved in 40 mL MeOH in a Parr hydrogenation bottle. A THF slurry of 10% Pd/C (0.57 g) is added. The mixture is hydrogenated for 45 min at 45 psi, recharging as needed. The mixture is filtered through a pad of Celite. The Celite is washed with excess MeOH. The solution is concentrated to give a solid and a yellow oil. The mixture is taken up in ether, filtered and concentrated to provide 16.2 g (90%) of 2-methylquinuclidin-3-one. MS (ESI) for C8H13NO m/z 140.2 (M+). The mixture is filtered through a pad of Celite The Celite is washed with excess MeOH The solution is concentrated to give a solid filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-Methylenequinuclidin-3-one (17.8 g, 0.1296 mol, 1 eq) is dissolved in 40 mL methanol in a Parr hydrogenation bottle. A THF slurry of 10% Pd/C (0.57 g) is added. The mixture is hydrogenated for 45 min at 45 psi, recharging as needed. The mixture is filtered through a pad of Celite. The Celite is washed with excess methanol. The solution is concentrated to give a solid and a yellow oil. The mixture is taken up in ether, filtered and concentrated to provide 16.2 g (90%) of 2-methylquinuclidin-3-one. MS (ESI) for C8H13NO m/z 140.2 (M+). The mixture is filtered through a pad of Celite The Celite is washed with excess methanol The solution is concentrated to give a solid filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-Methylenequinuclidin-3-one (17.8 g, 0.1296 mol, 1 eq) is dissolved in 40 mL MeOH in a Parr hydrogenation bottle. A THF slurry of 10% Pd/C (0.57 g) is added. The mixture is hydrogenated for 45 min at 45 psi, recharging as needed. The mixture is filtered through a pad of Celite. The Celite is washed with excess MeOH. The solution is concentrated to give a solid and a yellow oil. The mixture is taken up in ether, filtered and concentrated to provide 16.2 g (90%) of 2-methylquinuclidin-3-one. MS (ESI) for C8H13NO m/z 140.2 (M+). The mixture is filtered through a pad of Celite The Celite is washed with excess MeOH The solution is concentrated to give a solid filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-Methylenequinuclidin-3-one (17.8 g, 0.1296 mol, 1 eq) is dissolved in 40 mL MeOH in a Parr hydrogenation bottle. A THF slurry of 10% Pd/C (0.57 g) is added. The mixture is hydrogenated for 45 min at 45 psi, recharging as needed. The mixture is filtered through a pad of Celite. The Celite is washed with excess MeOH. The solution is concentrated to give a solid and a yellow oil. The mixture is taken up in ether, filtered and concentrated to provide 16.2 g (90%) of 2-methylquinuclidin-3-one. MS (ESI) for C8H13NO m/z 140.2 (M+). The mixture is filtered through a pad of Celite The Celite is washed with excess MeOH The solution is concentrated to give a solid filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-Methylenequinuclidin-3-one (17.8 g, 0.1296 mol, 1 eq) is dissolved in 40 mL MeOH in a Parr hydrogenation bottle. A THF slurry of 10% Pd/C (0.57 g) is added. The mixture is hydrogenated for 45 min at 45 psi, recharging as needed. The mixture is filtered through a pad of Celite. The Celite is washed with excess MeOH. The solution is concentrated to give a solid and a yellow oil. The mixture is taken up in ether, filtered and concentrated to provide 16.2 g (90%) of 2-methylquinuclidin-3-one. MS (ESI) for C8H13NO m/z 140.2 (M+). The mixture is filtered through a pad of Celite The Celite is washed with excess MeOH The solution is concentrated to give a solid filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 10.1 g (58.4 mmol) of 2-methylene-1-azabicyclo[2.2.2]octan-3-one hydrochloride hydrate, 8.1 g of K2CO3 and 100 mg of PtO2 in 100 mL of MeOH was hydrogenated at 10–15 psi H2 for about 1 hr. The solution was filtered through dicalite and the solvent was evaporated in vacuo. The residue was dissolved in CHCl3 and again filtered through dicalite. The filtrate was evaporated in vacuo to give 4.7 g (58% yield) of 2-methyl-1-azabicyclo[2.2.2]octan-3-one Compound 8A as a yellow oil. 1H NMR (CDCl3) 1.3 (d, 3H), 2.0 (m, 4H), 2.4 (t, 1H), 2.9 (m, 1H), 3.05 (, 1H), 3.2 (m, 3H). This material was used without further purification in the next step. The solution was filtered through dicalite the solvent was evaporated in vacuo The residue was dissolved in CHCl3 again filtered through dicalite The filtrate was evaporated in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-Methylenequinuclidin-3-one (17.8 g, 0.13 mol, 1 eq) is dissolved in 40 mL MeOH in a Parr hydrogenation bottle. A THF slurry of 10% Pd/C (0.57 g) is added. The mixture is hydrogenated for 45 min at 45 psi, recharging as needed. The mixture is filtered through a pad of Celite. The Celite is washed with excess MeOH. The solution is concentrated to give a solid and a yellow oil. The mixture is taken up in ether, filtered and concentrated to provide 16.2 g (90%) of 2-methylquinuclidin-3-one. MS (ESI) for C8H13NO m/z 140.2 (M+). The mixture is filtered through a pad of Celite The Celite is washed with excess MeOH The solution is concentrated to give a solid filtered concentrated