tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate Chemical Properties

Boiling point:

276℃

Density 

1.104

Flash point:

121℃

storage temp. 

2-8°C(protect from light)

pka

9.53±0.20(Predicted)

form 

solid

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

Safety Information

HS Code 

2933599590

tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate Usage And Synthesis

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.

Chemical Properties

6-(tert-butoxycarbonyl)-3,6-diazabicyclo[3.1.1]heptane is a white or off-white solid at room temperature and pressure, insoluble in water, and because of the molecule contains two nitrogen atoms, these nitrogen atoms can accept protons and show a certain degree of basicity. It is soluble in acidic aqueous solutions.

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

tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate(869494-16-6)Related Product Information

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