CATALYTIC HYDROGENATION OF METHYL 3,4-DIAZATRICYCLO-[5.2.1.0(2,6)]DEC-4-ENE-5-CARBOXYLATE

作者：Gorpinchenko V A; Petrov D V; Khursan S L; Dokichev V A^*; Tomilov Yu V

来源：Chemistry of Heterocyclic Compounds, 2009, 45(9): 1039-1046.

DOI：10.1007/s10593-009-0389-1

• 5-amino-exo-3-azatricyclo[5.2.1.0(2,6)]decane
• 5-amino-exo-3-azatricyclo[5.2.1.0(2,6)]decan-4-one
• methyl 3,4-diazatricyclo[5.2.1.0(2,6)]dec-4-ene-5-carboxylate
• Raney nickel
• catalytic hydrogenation

The hydrogenation at Raney nickel of the pyrazoline ring in methyl exo-3,4-diazatricyclo [5.2.1.0(2,6)] dec-4-ene-5-carboxylate takes place quantitatively with the preferential formation of the trans isomer of 5-amino-exo-3-azatricyclo[ 5.2.1.0(2,6)] decan-4-one. The 3-methoxycarbonylmethyl-, 3-acetyl-, and 3-nitroso-substituted esters are not hydrogenated under these conditions.

• 出版日期2009-9