Preparation of oxacycloalkenones
OwnerAryeh Frimerinventor
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Abstract
Oxacycloalkenones are prepared by reacting a cycloalkenone with a base in the presence of a dioxygen source in a suitable solvent and isolating the desired product. 1-Hydroxy 2-oxa-3-oxo-.DELTA..sup.4 steroids are convenient synthetic precursors to 2-oxa-3-oxo-.DELTA..sup.4 steroids which find use in modern clinical therapy.
Claims19
A process for the production of 1-hydroxy-2-oxa-3-oxo-.DELTA..sup.4 steroid which comprises contacting a 3-oxo-.DELTA..sup.4 steroid with a base in the presence of a dioxygen source in a suitable solvent and isolating the desired product.
A process for the production of 2-oxa-3-oxo-.DELTA..sup.4 steroid which comprises contacting a 3-oxo-.DELTA..sup.4 steroid with a base in the presence of a dioxygen source in a suitable solvent to produce a 1-hydroxy-2-oxa-3-oxo-.DELTA..sup.4 steroid, isolating the 1-hydroxy-2-oxa-3-oxo-.DELTA..sup.4 steroid, contacting the 1-hydroxy-2-oxa-3-oxo-.DELTA..sup.4 steroid with a metallic reducing agent and isolating the corresponding 2-oxa-3-oxo-.DELTA..sup.4 steroid.
A process for the production of 2-oxacholest-4-en-3-one which comprises the steps of contacting cholest-4-en-3-one with potassium superoxide in benzene containing 18-crown-6, reacting the resulting 1-hydroxy-2-oxacholest-4-en-3-one with sodium borohydride, and isolating the 2-oxacholest-4-en-3-one.
A process for the production of 2-oxatestosterone which comprises the steps of contacting testosterone with potassium superoxide in benzene containing 18-crown-6, reacting the resulting 1-hydroxy-2-oxatestosterone with sodium borobydride, and isolating the 2-oxatestosterone.
Dependencies are inferred from the claim text.