PURPOSE: To industrially and advantageously prepare the compounds each of which consists of an enol ether of 3-keto-16β-methyl- or 16-methyl-16- methoxyoxalyl-steroid and is useful as a raw material for preparing an anti- inflammatory corticoid, or the like.
CONSTITUTION: The preparation of such an objective steroid intermediate compound represented by the formula (wherein: R16 and R16' are a β-methyl group and H respectively, or a methyl group and a methoxyoxalyl group respectively; and the dotted line indicates a double bond when R16 and R16' are a β-methyl group and H respectively, or a single bond when R16 and R16' are a methyl group and a methoxyoxalyl group respectively), comprises: cooling 3- methoxyandrosta-3,5,9(11)-trien-17-one, together with methyl chloride and diethyl oxalate, to 0°C; adding solid sodium methoxide to the cooled substance to allow them to react with each other and to form a sodium salt of 3-methoxy-16- methyl-16-(methoxyoxalyl)androsta-3,5,9(11)-trien-17-one; thereafter, adding acetone to the resulting compound to form a dilute slurry of the compound; and then, adding methyl iodide to the slurry to allow them to react with each other at 65°C for 18 hr.
JIYOSEFU MAIKERU TEMUKO
JPS53127455A | 1978-11-07 |