tert-butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate Chemical Properties

Boiling point:

295.4±15.0 °C(Predicted)

Density 

1.076

storage temp. 

2-8°C(protect from light)

pka

9.80±0.20(Predicted)

form 

solid

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

Safety Information

HS Code 

2933998090

tert-butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate Usage And Synthesis

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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