Exemestane Impurity 11 synthesis

Yield:-

Reaction Conditions:

with hydrogenchloride in acetic acid;

Steps:

3 EXAMPLE 3

EXAMPLE 3 A solution of 4,5-epoxy-6-methylenandrost-1-ene-3,17-dione (1.0 g) in glacial acetic acid (10 ml) was treated with gaseous hydrogen chloride for 30 min at room temperature The precipitate was filtered off, washed with diethyl ether, dried and chromatographed on silica gel using hexane/ethyl acetate to yield 0.8 g of pure 4-chloro-6-methylenandrosta-1,4-diene-3,17-dione. Found: C 72.40, H 6.91, Cl 10.53; C₂₀ H₂₃ ClO₂ requires: C 72.61, H 7.01, Cl 10.72. N.M.R. δp.p.m.: 0.84 (3H, s); 1.24 (3H, s); 5.13 (1H, s); 5.43 (1H, s); 6.37 (1H, d); 7.08 (1H, d). MS (m/z): 330.

References:

US4808616,1989,A