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

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)

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