Process for the preparation of 17(20)ene-21-steroid aldehydes
AssigneeResearch Corporation
InventorsKathlyn A. Parker, Raymond W. Kosley, Jr.
Life of this patent
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Abstract
There is disclosed a process for the efficient conversion of 17-.alpha.-ethynyl 17-.beta.- hydroxy steroids into the corresponding 17(20) .alpha..beta.-unsaturated 21-steroid aldehydes. The process comprises the sequential steps of reacting the ethynyl alcohol with a diloweralkylformamide dilower-alkylacetal, suitably dimethylformamide diethylacetal, to form the corresponding 16,20 diene-21-diloweralkylamine which is then hydrolyzed to form the corresponding 17(20)-ene-21-steroid aldehyde.
Claims18
A process which comprises reacting a cyclopenta deca hydro(a)naphthalene of the formula ##STR7## wherein --Z-- is a carbon carbon single bond or a carbon carbon double bond and q is selected from the group consisting of ##STR8## where R.sub.1 is lower alkyl, phenyl or phenyl loweralkyl, R.sub.2 is loweralkyl
- provided that where q is ##STR9## z is a carbon carbon double bond and for the other values of q, z is a carbon carbon single bond with an excess of a diloweralkyl formamide diloweralkylacetal, wherein the term loweralkyl indicates an alkyl moiety of 1 to 5 carbon atoms ##STR10## where R.sub.3 and R.sub.4 are loweralkyl and may be the same or different to yield the corresponding dienamine of the formula ##STR11##
A process which comprises reacting a cyclopenta deca hydro(a)naphthalene of the formula ##STR13## wherein --Z-- is a carbon carbon single bond or a carbon carbon double bond and q is selected from the group consisting of ##STR14## where R.sub.1 is lower alkyl, phenyl or phenyl loweralkyl, R.sub.2 is loweralkyl
- provided that where q is ##STR15## z is a carbon carbon double bond and for the other values of q, z is a carbon carbon single bond with an excess of a diloweralkyl formamide diloweralkylacetal wherein the term loweralkyl indicates an alkyl moiety of 1 to 5 carbon atoms ##STR16## where R.sub.3 and R.sub.4 are loweralkyl and may be the same on different to yield the corresponding dienamine of the formula ##STR17## and hydrolyzing with a hydrolyzing agent selected from the group consisting of water, mild base and mild acid said dienamine to yield the corresponding alpha beta unsaturated aldehyde of the formula ##STR18##
An alpha beta unsaturated aldehyde having the formula ##STR24##
Dependencies are inferred from the claim text.