Tert-butyl 2,5-diazabicyclo[2.2.2]octane-2-carboxylate Chemical Properties

Boiling point:

295.4±15.0 °C(Predicted)

Density 

1.076±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

9.72±0.20(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C11H20N2O2/c1-11(2,3)15-10(14)13-7-8-4-5-9(13)6-12-8/h8-9,12H,4-7H2,1-3H3

InChIKey

RBLOMFQUEUBEBG-UHFFFAOYSA-N

SMILES

C12CCC(NC1)CN2C(OC(C)(C)C)=O

Safety Information

HS Code 

2933998090

Tert-butyl 2,5-diazabicyclo[2.2.2]octane-2-carboxylate Usage And Synthesis

Uses

Tert-butyl 2,5-diazabicyclo[2.2.2]octane-2-carboxylate can be used as a reagent for organic synthesis or as a pharmaceutical intermediate in the preparation of active biomolecular inhibitors.

Synthesis

The general procedure for the synthesis of tert-butyl 2,5-diazabicyclo[2.2.2]octane-2-carboxylate from di-tert-butyl dicarbonate (6.5 mmol) and 2,5-diazabicyclo[2.2.2]octane dihydrochloride (7.06 mmol) is as follows: a solution of isopropanol (15 mL) of di-tert-butyl dicarbonate is slowly added dropwise to a solution of isopropanol (100 mL), water (35 mL), and 1M sodium hydroxide solution (6.5 mL) at 0°C, containing 2,5-diazabicyclo[2.2.2]octane dihydrochloride. bicyclo[2.2.2]octane dihydrochloride in a mixture of isopropanol (100 mL), water (35 mL) and 1M sodium hydroxide solution (6.5 mL). The reaction mixture was stirred at 0°C for 1.5 h and then concentrated to about 50 mL. Subsequently, the aqueous phase was saturated with solid sodium chloride and the pH was adjusted to 10 with 2 M sodium hydroxide solution. the aqueous phase was extracted with ethyl acetate (3 x 35 mL) and the combined organic layers were washed with brine and dried with magnesium sulfate. Finally, the solvent was removed by distillation under reduced pressure to afford the crude product tert-butyl 2,5-diazabicyclo[2.2.2]octane-2-carboxylate in 42% yield as a light yellow oil.

References

[1] Patent: WO2005/63767, 2005, A2. Location in patent: Page/Page column 52

Tert-butyl 2,5-diazabicyclo[2.2.2]octane-2-carboxylate(858671-91-7)Related Product Information

• (S)-3-N-Boc-aminopiperidine
• (R)-1-Boc-3-Aminopiperidine
• 2,5-Diazabicyclo[2.2.2]octane
• METHYL-3-PIPERIDINYL-CARBAMIC ACID ETHYL ESTER
• (R)-PIPERIDIN-2-YLMETHYL-CARBAMIC ACID TERT-BUTYL ESTER
• 3-N-BOC-3-(METHYLAMINO)PIPERIDINE
• 2-(Boc-aminomethyl)-piperidine
• 2,5-DIAZA-BICYCLO[2.2.2]OCTANE-2-CARBOXYLIC ACID TERT-BUTYL ESTER
• (R)-3-N-Boc-3-(methylamino)piperidine
• (R)-1-N-BOC-3-METHYLAMINO PIPERIDINE
• (R)-2-AMINOMETHYL-1-N-BOC-PIPERIDINE
• (2S,5S)-2,5-DIMETHYL-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER