| Identification | Back Directory | [Name]
3,6-Diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester | [CAS]
869494-16-6 | [Synonyms]
3,6-DiazabicycL
o[3.1.1]heptane-6-carboxyL
6-Boc-3,6-diaza-bicyclo[3.1.1]heptane
tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate
6-(tert-Butyloxycarbonyl)-3,6-diazabicyclo[3.1.1]heptane
tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate 97%
(1R,5S)-tert-butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate
tert-Butyl (1S,5R)-3,6-diazabicyclo[3.1.1]heptane-6-carboxylate
3,6-Diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester
3,6-Diazabicyclo[3.1.1]heptane-6-carboxylic acid, 1,1-dimethylethyl ester
3,?6-?Diazabicyclo[3.1.1]?heptane-?6-?carboxylic acid, 1,?1-?dimethylethyl ester
869494-16-6 | [Molecular Formula]
C10H18N2O2 | [MDL Number]
MFCD17016736 | [MOL File]
869494-16-6.mol | [Molecular Weight]
198.26 |
| Chemical Properties | Back Directory | [Boiling point ]
276℃ | [density ]
1.104 | [Fp ]
121℃ | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [form ]
solid | [pka]
9.53±0.20(Predicted) | [color ]
White to off-white | [InChI]
InChI=1S/C10H18N2O2/c1-10(2,3)14-9(13)12-7-4-8(12)6-11-5-7/h7-8,11H,4-6H2,1-3H3 | [InChIKey]
OUFBVDKNEWUFHP-UHFFFAOYSA-N | [SMILES]
C12CC(N1C(OC(C)(C)C)=O)CNC2 |
| Questions And Answer | Back Directory | [Uses]
6-(tert-Butoxycarbonyl)-3,6-diazabicyclo[3.1.1]heptane can be used as an organic synthesis intermediate, primarily for synthesizing piperidine drug molecules with a bridged bicyclic structure. Bridging bicyclic piperazines is an important component in medicinal chemistry research. Among them, the bicyclic piperazine 6-(tert-Butoxycarbonyl)-3,6-diazabicyclo[3.1.1]heptane is achiral, and based on its cLogP derivative analogues, it exhibits lipophilicity similar to piperazines, making it a suitable starting material for the synthesis of various drugs. |
| Hazard Information | Back Directory | [Synthesis]
To a stirred solution of 3,6-Diazabicyclo[3.1.1]heptane-6-carboxylic acid, 3-[(2-nitrophenyl)sulfonyl]-, 1,1-dimethylethyl ester (400 mg, 1.04 mmol) in DMF (2.5 mL) were added dodecanethiol (500 μL, 2.09 mmol) and lithium hydroxide hydrate (88 mg, 2.09 mmol). The mixture was stirred at r.t. for 2 h. The mixture was diluted with hexanes-ethyl acetate (10 mL, 1:1). The mixture was extracted with aq. Hydrochloric acid (2 x 5.0 mL). The aq. layer was extracted with hexanes-ethyl acetate (10 mL, 1:1). The combined organic layers were discarded. The aq. layer was basified with NaOH (6.0 mL of 1.0 M solution) until pH=13. The aq. layer was extracted with methylene chloride-methanol (2 x 10 mL, 9:1). The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate as a white solid; Yield, 167 mg (81percent)
| [References]
[1] Tetrahedron Letters, 2012, vol. 53, # 47, p. 6332 - 6334 |
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