Process for the preparation of 1-hydroxylated vitamin D compound

Details Process for the preparation of 1-hydroxylated vitamin D compound Process for the preparation of 1-hydroxylated vitamin D compound

1984-09-07

1985-11-19

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07J 900

Patent

active

045541051

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.

REFERENCES:
patent: 4202829 (1980-05-01), De Luca et al.
patent: 4297289 (1981-10-01), De Luca et al.
patent: 4338250 (1982-07-01), De Luca et al.
Synthesis of Calcitroic Acid, Metabolite of 1 25-Dihydroxychlocecalciferol, Robert P. Esvelt, et al., Journal Organic Chemistry, 1981, vol. 46, pp. 456-458.
A Stereocontrolled Partial Synthesis of 1 -Hydroxy Vitamin D.sub.3, Luc J. Vanmaele, et al., Tetrahedron Letters, vol. 23, No. 9, pp. 995-998, 1982.
Selenium Dioxide Oxidation of Cholecalciferol, Bohumil Pelc, Steroids, vol. 30, No. 2, Aug. 1977, pp. 193-201.
Direct C-1 Hydroxylation of Vitamin D compounds: Convenient Preparation of 1-Hydroxyvitamin D.sub.3, 1 25-Dihydroxyvitamin D.sub.3, and 1-Hydroxyvitamin D.sub.2, Herbert F. Deluca, Proceedings National Academy of Science, U.S.A., vol. 75, No. 5, pp. 2080-2081, May 1978.
Direct C (1) Hydroxylation of Vitamin D.sub.3 and Related Compounds, Herbert E. Paaren, et al., Journal Organic Chemistry, 1980, 45, pp. 3253-3258.

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