tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride Chemical Properties

Boiling point:

276.4±15.0 °C(Predicted)

Density 

1.104±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

9.74±0.20(Predicted)

form 

solid

color 

White

optical activity

Consistent with structure

InChI

InChI=1S/C10H18N2O2/c1-10(2,3)14-9(13)12-6-7-4-8(12)5-11-7/h7-8,11H,4-6H2,1-3H3/t7-,8-/m1/s1

InChIKey

UXAWXZDXVOYLII-HTQZYQBOSA-N

SMILES

[C@@]12([H])C[C@@]([H])(NC1)CN2C(OC(C)(C)C)=O

Safety Information

WGK Germany 

3

HS Code 

2933998090

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride Usage And Synthesis

Uses

(1R,4R)-5-Boc-2,5-diazabicyclo[2.2.1]heptane is a useful reagent employed in the preparation of tetrahydroisoquinolines as CXCR4 antagonists.

Synthesis

Example 15B: Synthesis of tert-butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate The product of Example 15A, (1R,4R)-5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (2 g, 6.9 mmol) was dissolved in 50 mL of ethanol and 10% Pd/C catalyst (150 mg) was added. The reaction was stirred under hydrogen atmosphere (1 atm) for 16 hours. After completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to give the white solid product tert-butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1.28 g, 93.4% yield). Product characterization data: 1H NMR (DMSO-d6, MHz) δ 1.39 (s, 9H), 1.54 (d, J = 5.6 Hz, 1H), 1.58 (t, J = 9.5 Hz, 1H), 2.70-2.81 (m, 2H), 3.17 (m, 1H), 3.50 (s, 1H), 4.17 (d, J = 10.17 Hz, 1H). MS (DCI/NH3) m/z 199 (M + H)+, 216 (M + NH4)+.

References

[1] Patent: EP1147112, 2003, B1. Location in patent: Page/Page column 19
[2] Patent: US2003/225268, 2003, A1. Location in patent: Page 21
[3] Patent: US2005/101602, 2005, A1. Location in patent: Page/Page column 37
[4] RSC Advances, 2015, vol. 5, # 14, p. 10386 - 10392
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3627 - 3644

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride(134003-84-2)Related Product Information

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