| Identification | Back Directory | [Name]
tert-butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate | [CAS]
201162-53-0 | [Synonyms]
3-Boc-3,8-diaza-bicyclo[3...
3-Boc-3,8-diazabicyclo[3.2.1]octane
3,8-Diazabicyclo[3.2.1]octane,N-BOCprotected
tert-butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylat
tert-butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate
3,8-Diazabicyclo[3.2.1]octane-3-carboxylic acid tert-butyl ester
3,8-Diazabicyclo[3.2.1]octane-3-carboxylic acid, 1,1-dimethylethyl ester | [Molecular Formula]
C11H20N2O2 | [MDL Number]
MFCD11111771 | [MOL File]
201162-53-0.mol | [Molecular Weight]
212.291 |
| Chemical Properties | Back Directory | [Boiling point ]
295.4±15.0 °C(Predicted) | [density ]
1.076 | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [form ]
solid | [pka]
9.80±0.20(Predicted) | [color ]
White | [InChI]
InChI=1S/C11H20N2O2/c1-11(2,3)15-10(14)13-6-8-4-5-9(7-13)12-8/h8-9,12H,4-7H2,1-3H3 | [InChIKey]
PSDAEKDIOQXLLC-UHFFFAOYSA-N | [SMILES]
C12NC(CC1)CN(C(OC(C)(C)C)=O)C2 |
| Hazard Information | Back Directory | [Uses]
tert-Butyl 3,8-Diazabicyclo[3.2.1]octane-3-carboxylate is used in preparation of substituted pyrrolo[2,3-b]pyridines for suppressing toxic endoplasmic reticulum stress. | [Synthesis]
The general procedure for the synthesis of tert-butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate from tert-butyl 8-benzyl-3,8-diazabicyclo[3.2.1]octane-3-carboxylate was as follows: the product of Example 23A (0.62 g, 0.12 mmol) was dissolved in ethanol (10 mL) and palladium/carbon (Aldrich, 60 mg, 10 wt%) as a catalyst. The reaction was stirred at room temperature for 18 h under an atmosphere of hydrogen (balloon) at 1 atm. Upon completion of the reaction, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by silica gel column chromatography with an eluent ratio of 1% ammonia:9% methanol:90% dichloromethane to afford tert-butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate, the target compound (0.44 g, 100% yield). Mass spectral analysis (DC1/NH3) showed m/z 213 (M + H)+. | [References]
[1] Journal of Medicinal Chemistry, 1998, vol. 41, # 5, p. 674 - 681
[2] Patent: US2005/101602, 2005, A1. Location in patent: Page/Page column 35
[3] Patent: US2005/9841, 2005, A1. Location in patent: Page/Page column 16
[4] Patent: US2005/80095, 2005, A1. Location in patent: Page/Page column 19 |
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