ChemicalBook CAS DataBase List tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride

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

8synthesis methods

Product Name:tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride
CAS Number:134003-84-2
Molecular formula:C10H18N2O2
Molecular Weight:198.26

(1R,4R)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

134003-83-1
26 suppliers
$190.00/1g

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

134003-84-2
100 suppliers
$45.00/100mg

Yield:134003-84-2 93.4%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethanol under 760.051 Torr; for 16 h;

Steps:

15.B tert-butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
Example 15B tert-butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate The product from Example 15A (2 g, 6.9 mmol) in 50 mL of EtOH was treated with 10% Pd/C (150 mg) under an H₂ atmosphere (1 atm) for 16 hours. The mixture was filtered and the solvent was evaporated under reduced pressure to yield 1.28 g (93.4 %) of the title compound. 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, H), 2.70-2.81 (M, 2H), 3.50 (dd, J=1.02, 10.50, 1H), 3.17 (m, 1H), 3.50 (s, 1H), 4.17 (d, J=10.17 Hz, H); MS (DCI/NH₃) m/z 199 (M+H)⁺, 216 (M+NH₄)⁺.

References:

ABBOTT LABORATORIES EP1147112, 2003, B1 Location in patent:Page/Page column 19

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