Process for the preparation of 1-hydroxylated vitamin D compounds
AssigneeResearch Institute for Medicine and Chemistry Inc.
InventorRobert H. Hesse
Life of this patent
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Abstract
1-unsubstituted 5,6-trans vitamin D compounds are 1.alpha.-hydroxylated by Se.sup.IV oxidation in the presence of selenous acid at a pH in the range 3-9. The oxidation is preferably effected using a 1-unsubstituted-3-trihydrocarbylsilyloxy-5,6-trans vitamin D compound in the presence of a co-oxidant.
Claims10
A process for the 1.alpha.-hydroxylation of vitamin D compounds by SE.sup.IV oxidation which comprises the oxidation of a 1-unsubstituted 5,6-trans vitamin D compound of formula I:
- ##STR7## wherein Y represents a hydrogen atom, a hydroxyl group, an alkanoyloxy group having 1 to 6 carbon atoms, an aroyloxy group having 7 to 15 carbon atoms, a lower alkoxy group having 1 to 6 carbon atoms which may be interrupted by an oxygen atom, a tetrahydropyranyloxy group or a trihydrocarbylsilyloxy group and R represents a group of the formula:- ##STR8## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.5 which may be the same or different, each represents a hydrogen or halogen atom, a hydroxy group, an alkanoyloxy group having 1 to 6 carbon atoms, an aroyloxy group having 7 to 15 carbon atoms, a lower alkoxy group having 1 to 6 carbon atoms which may be interrupted by an oxygen atom, a tetrahydropyranyloxy group or a trihydrocarbylsilyloxy group, or R.sup.1 and R.sup.2 may together form a carbon-carbon bond or an epoxy group;
- R.sup.4 represents a hydrogen or halogen atom or a methyl or ethyl group, or R.sup.3 and R.sup.4 together represent a keto or protected keto group;
- and R.sup.6 represents a hydroxy or hydrocarbylsulphonyloxy group in the presence of a selenous acid at a pH in the range 3-9.
A process as claimed in claim 4 wherein the oxidation is effected by the use of selenium dioxide and water, the ratio of selenium dioxide to water being in the range 0.1 to 50 by weight.
Dependencies are inferred from the claim text.