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CC1C(=O)C2CCN1CC2Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-methyl-1-azabicyclo[2.2.2]octan-3-one |
|---|---|
| IUPAC Name | — |
| CAS Number | 5291-14-5 |
| Database ID | 12381698 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-methyl-1-azabicyclo[2.2.2]octan-3-one (CAS 5291-14-5) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 12381698
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-62a75198d1b645c593655217d1097307Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-55aef60758c048e8bdd703b2ac135781Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-93b7fa5c6709475791ec2dd5950ebd40Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-792eb4da0400464d89265b76b39e9b72Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-dcc4f9d586d94235b4790ce949c04575Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-f8b9486948834d90a0eb4d2c9ca603e2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-c76feb3475e144eb9de8c2620f37ec19Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-54ef82d8f6a34e56ae897cd8c926fba4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-54ef82d8f6a34e56ae897cd8c926fba4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-d078592b39b14c47a1912f2b8c155eeaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-dcc4f9d586d94235b4790ce949c04575Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-f8b9486948834d90a0eb4d2c9ca603e2PubChem References
These sources are listed in the compound's public database record.
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