No renderable structure data available
CC(C)(C)OC(=O)N1C2CCC1C(=O)NC2Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tert-butyl 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylate |
|---|---|
| IUPAC Name | — |
| CAS Number | 1622919-66-7 |
| Database ID | 16638505 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tert-butyl 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (CAS 1622919-66-7) 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 16638505
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
10 reactions · 10 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-950f235e72fd45e39128869ebfaeaaabConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (108 mg, 0.48 mmol) in DCM (0.5 mL) at 0° C. was added dropwise, TFA (0.5 ml) and the reaction mixture stirred for 30 min. The reaction was warmed to RT and stirred for 1 h before being concentrated in vacuo and triturated with diethyl ether. The resultant residue was subjected to flash chromatography (Isolute NH2, 50% methanol in DCM) to give 3,8-Diaza-bicyclo[3.2.1]octan-2-one as a white solid (69 mg, quantitative). LCMS): RT=0.32 min, [M+H]+=127. 1H NMR 400 MHz (DMSO-d6) δ: 7.02 (1H, br, s), 3.53 (1H, m), 3.24 (1H, dd, J=11.00, 4.14 Hz), 2.80-2.79 (1H, m), 2.77 (1H, m), 1.78 (3H, m), 1.57-1.56 (1H, m). before being concentrated in vacuo triturated with diethyl ether
Source ID: ord-59bd65ab7c2e4cbf94dd2da163aeddafConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (108 mg, 0.48 mmol) in DCM (0.5 mL) at 0° C. was added dropwise, TFA (0.5 ml) and the reaction mixture stirred for 30 min. The reaction was warmed to RT and stirred for 1 h before being concentrated in vacuo and triturated with diethyl ether. The resultant residue was subjected to flash chromatography (Isolute NH2, 50% methanol in DCM) to give 3,8-Diaza-bicyclo[3.2.1]octan-2-one as a white solid (69 mg, quantitative). LCMS): RT=0.32 min, [M+H]+=127. 1H NMR 400 MHz (DMSO-d6) δ: 7.02 (1H, br, s), 3.53 (1H, m), 3.24 (1H, dd, J=11.00, 4.14 Hz), 2.80-2.79 (1H, m), 2.77 (1H, m), 1.78 (3H, m), 1.57-1.56 (1H, m). before being concentrated in vacuo triturated with diethyl ether
Source ID: ord-59bd65ab7c2e4cbf94dd2da163aeddafConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-950f235e72fd45e39128869ebfaeaaabConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (108 mg, 0.48 mmol) in DCM (0.5 mL) at 0° C. was added dropwise, TFA (0.5 ml) and the reaction mixture stirred for 30 min. The reaction was warmed to RT and stirred for 1 h before being concentrated in vacuo and triturated with diethyl ether. The resultant residue was subjected to flash chromatography (Isolute NH2, 50% methanol in DCM) to give 3,8-Diaza-bicyclo[3.2.1]octan-2-one as a white solid (69 mg, quantitative). LCMS): RT=0.32 min, [M+H]+=127. 1H NMR 400 MHz (DMSO-d6) δ: 7.02 (1H, br, s), 3.53 (1H, m), 3.24 (1H, dd, J=11.00, 4.14 Hz), 2.80-2.79 (1H, m), 2.77 (1H, m), 1.78 (3H, m), 1.57-1.56 (1H, m). before being concentrated in vacuo triturated with diethyl ether
Source ID: ord-25110d3f73bc4e28b2c4f2352cd52fffConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following general N—C coupling procedure 1, 5-bromo-2-nitropyridine (110 mg, 0.542), was combined with 2-Oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (135 mg, 0.596 mg), which after purification silica gel chromatography gave 3-(6-Nitro-pyridin-3-yl)-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (290 mg, 81%). MS m/z 349.0 (MH+), and was used directly as is without further characterization. after purification silica gel chromatography
Source ID: ord-45a2cde6055041beb8857881393defdbConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (108 mg, 0.48 mmol) in DCM (0.5 mL) at 0° C. was added dropwise, TFA (0.5 ml) and the reaction mixture stirred for 30 min. The reaction was warmed to RT and stirred for 1 h before being concentrated in vacuo and triturated with diethyl ether. The resultant residue was subjected to flash chromatography (Isolute NH2, 50% methanol in DCM) to give 3,8-Diaza-bicyclo[3.2.1]octan-2-one as a white solid (69 mg, quantitative). LCMS): RT=0.32 min, [M+H]+=127. 1H NMR 400 MHz (DMSO-d6) δ: 7.02 (1H, br, s), 3.53 (1H, m), 3.24 (1H, dd, J=11.00, 4.14 Hz), 2.80-2.79 (1H, m), 2.77 (1H, m), 1.78 (3H, m), 1.57-1.56 (1H, m). before being concentrated in vacuo triturated with diethyl ether
Source ID: ord-95f01a8e237e43c2942580d5753bae99Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (108 mg, 0.48 mmol) in DCM (0.5 mL) at 0° C. was added dropwise, TFA (0.5 ml) and the reaction mixture stirred for 30 min. The reaction was warmed to RT and stirred for 1 h before being concentrated in vacuo and triturated with diethyl ether. The resultant residue was subjected to flash chromatography (Isolute NH2, 50% methanol in DCM) to give 3,8-Diaza-bicyclo[3.2.1]octan-2-one as a white solid (69 mg, quantitative). LCMS): RT=0.32 min, [M+H]+=127. 1H NMR 400 MHz (DMSO-d6) δ: 7.02 (1 H, br, s), 3.53 (1 H, m), 3.24 (1 H, dd, J=11.00, 4.14 Hz), 2.80-2.79 (1 H, m), 2.77 (1 H, m), 1.78 (3 H, m), 1.57-1.56 (1 H, m). before being concentrated in vacuo triturated with diethyl ether
Source ID: ord-f693e01ac4df4d389c44d77236245e18Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (108 mg, 0.48 mmol) in DCM (0.5 mL) at 0° C. was added dropwise, TFA (0.5 ml) and the reaction mixture stirred for 30 min. The reaction was warmed to RT and stirred for 1 h before being concentrated in vacuo and triturated with diethyl ether. The resultant residue was subjected to flash chromatography (Isolute NH2, 50% methanol in DCM) to give 3,8-Diaza-bicyclo[3.2.1]octan-2-one as a white solid (69 mg, quantitative). LCMS): RT=0.32 min, [M+H]+=127. 1H NMR 400 MHz (DMSO-d6) δ: 7.02 (1 H, br, s), 3.53 (1 H, m), 3.24 (1 H, dd, J=11.00, 4.14 Hz), 2.80-2.79 (1 H, m), 2.77 (1 H, m), 1.78 (3 H, m), 1.57-1.56 (1 H, m). before being concentrated in vacuo triturated with diethyl ether
Source ID: ord-6ba0be93e1c542baa8e640643092c7a0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (108 mg, 0.48 mmol) in DCM (0.5 mL) at 0° C. was added dropwise, TFA (0.5 ml) and the reaction mixture stirred for 30 min. The reaction was warmed to RT and stirred for 1 h before being concentrated in vacuo and triturated with diethyl ether. The resultant residue was subjected to flash chromatography (Isolute NH2, 50% methanol in DCM) to give 3,8-Diaza-bicyclo[3.2.1]octan-2-one as a white solid (69 mg, quantitative). LCMS): RT=0.32 min, [M+H]+=127. 1H NMR 400 MHz (DMSO-d6) δ: 7.02 (1H, br, s), 3.53 (1H, m), 3.24 (1H, dd, J=11.00, 4.14 Hz), 2.80-2.79 (1H, m), 2.77 (1H, m), 1.78 (3H, m), 1.57-1.56 (1H, m). before being concentrated in vacuo triturated with diethyl ether
Source ID: ord-59bd65ab7c2e4cbf94dd2da163aeddafPubChem References
These sources are listed in the compound's public database record.
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