N-Boc-9-azabicyclo[3.3.1]nonan-3-one Chemical Properties

Boiling point:

342.9±35.0 °C(Predicted)

Density 

1?+-.0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-1.65±0.20(Predicted)

form 

solid

color 

white

InChI

InChI=1S/C13H21NO3/c1-13(2,3)17-12(16)14-9-5-4-6-10(14)8-11(15)7-9/h9-10H,4-8H2,1-3H3

InChIKey

YEKYAQUJESJBFI-UHFFFAOYSA-N

SMILES

C12N(C(OC(C)(C)C)=O)C(CCC1)CC(=O)C2

Safety Information

HS Code 

2933998090

N-Boc-9-azabicyclo[3.3.1]nonan-3-one Usage And Synthesis

Synthesis

General procedure for the synthesis of N-Boc-9-azabicyclo[3.3.1]nonan-3-one hydrochloride from di-tert-butyl dicarbonate and 9-azabicyclo[3.3.1]nonan-3-one hydrochloride: 9-azabicyclo[3.3.1]nonan-3-one hydrochloride (12.0 g, 68.3 mmol) was suspended in tetrahydrofuran (THF, 200 mL) followed by addition of methylamine (27.6 g, 273 mmol). Di-tert-butyl dicarbonate (15.6 g, 71.7 mmol) dissolved in THF (50 mL) was added slowly and dropwise over 15 min at 15 °C. The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, water was added and extracted with diethyl ether (200 mL). The organic phase was washed with water (2 x 100 mL) and subsequently purified by filtration through a short silica gel column. The final product N-Boc-9-azabicyclo[3.3.1]nonan-3-one was obtained in a yield of 15.24 g (93% yield).

References

[1] Patent: WO2009/98209, 2009, A1. Location in patent: Page/Page column 16

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