Process improvements in steroid chemistry

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C552S612000

Reexamination Certificate

active

06982329

ABSTRACT:
Steroids containing a cyclohexene moiety are efficiently oxidized to the corresponding α,β-unsaturated ketone using copper iodide and t-butyl hydroperoxide. A steroid compound containing the α,β-unsaturated ketone structure is efficiently converted to the corresponding vicinal diol using a hydroborating reagent followed by oxidative workup, e.g., borane followed by sodium perborate. Benzoyl and substituted benzoyls are superior protecting groups for hydroxyl groups present in the compounds.

REFERENCES:
patent: 5869709 (1999-02-01), Marwah et al.
patent: 6046185 (2000-04-01), Burgoyne et al.
patent: 6252119 (2001-06-01), Salvador et al.
patent: WO 98/02450 (1998-01-01), None
patent: WO 01/83512 (2001-11-01), None
Salvador et al., “Copper-Catalysed Allylic Oxidation of 5-ene-Steroids by t-butyl Hydroperoxide.”, Tetrahedron Letters, vol. 38(1), pp. 119-122, 1997.
Brown et al., “Hydroboration. XXVI. The hydroboration of 2-Butenyl (Crotyl) and related derivatives containing representative substituents. Control of the elimination reaction of α-substituted organoboranes,”Journal of the American Chemical Society90(11):2906-2915, May 22, 1968.
Jung et al., “First total synthesis of estobergsterol A and active structural analogues of the xestobergsterols,”Tetrahedron57(8):1449-1481, Feb. 18, 2001.
Krafft et al., “Synthesis of the C/D/E and A/B rings of Xestobergsterol-(A)”Journal of Organic Chemistry64(7):2475-2485, 1999.
Neves et al., “Improved syntheses of aromatase inhibitors and neuroactive steroids efficient oxidations and reductions at key positions for bioactivity,”Tetrahedron55(11):3255-3264, Mar. 1999.
Salvador et al., “Copper-catalysed allylic oxidation of δ-5-steroids by t-butyl-hydroperoxide,”Tetrahedron Letters38 (1):119-122, 1997.
Dauben et al. “Allylic Oxidation of Olefins with Chromium Trioxide-Pyridine Complex,”Journal of Organic Chemistry34 (11):3587-3592, Nov. 1969.
Jerry March,Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4thEd., John Wiley & Sons, New York, 1992, Chap. 5-12 & 5-13, pp. 783-790.
Jerry March,Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4thEd., John Wiley & Sons, New York, 1992, Chap. 5-35, pp. 822-825.
Jerry March,Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4thEd., John Wiley & Sons, New York, 1992, Chap. 19, “Oxidations and Reductions”, pp. 1158-1238.
Miller et al. “A Ruthenium Catalyzed Oxidation of Steroidal Alkenes to Enones,”Tetrahedron Letters37(20):3429-3432, 1996.

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