| Identification | Back Directory | [Name]
tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride | [CAS]
134003-84-2 | [Synonyms]
(1R,4R)
(1R,4R)-5-Boc-2,5-diazabicyclo[2.2.1]heptane
(1R,4R)-5-N-Boc-2,5-diazabicyclo[2.2.1]heptane
(1R,4R)-2-Boc- 2,5-diazabicyclo[2.2.1]heptane-HCl
tert-Butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
(1R,4R)-tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride
1,1-Dimethylethyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
(1R,4R)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester
tert-butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride
(1R,4R)-tert-butyl 2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate HCl 134003-84-2
2,5-Diazabicyclo[2.2.1]heptane-2-carboxylic acid, 1,1-dimethylethyl ester, (1R,4R)- | [Molecular Formula]
C10H18N2O2 | [MDL Number]
MFCD01321293 | [MOL File]
134003-84-2.mol | [Molecular Weight]
198.26 |
| Chemical Properties | Back Directory | [Boiling point ]
276.4±15.0 °C(Predicted) | [density ]
1.104±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [form ]
solid | [pka]
9.74±0.20(Predicted) | [color ]
White | [Optical Rotation]
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 |
| Hazard Information | Back Directory | [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 |
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