PURPOSE: To efficiently obtain the compound, which is used as aromatase inhibitor, by allowing 19-norandrost-5(10)-ene-3,17-dione to react by turns with diol, N-halosuccinicamide and silyl-2-propinyl Cu salt.
CONSTITUTION: 19-Norandrost-5-(10)-ene-3,17-dione of formula I is allowed to react with 2,2-dimethyl-1,3-propandiol and trimethyl-orthoformate in the presence of strong acid in a solvent so as to produce bis-gem-dimethyldioxan, and then allowed to react with N-bromosuccinimide to produce a bromohydrin derivative, and this derivatives is epoxidized with a strong base, and then allowed to react with trialkylsilyl protected 2-propynyl Cu salt to produce bis-gem-dimethylketal, and further treated with a dehindering reagent so that the objective product of 10-(2-propynyl)estr-4-ene-3,17-dione of formula II is obtained.
HAABEI DEII BENSON
SHINSHIA RUSHIIRU RANDO
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