Claims
- 1. A process for preparing a 17.alpha.-(2-R-ethynyl-17.beta.-hydroxysteroido[2,3-d]isoxazole which comprises reacting a 17-oxosteroido[2,3-d]isoxadole devoid of substituents, other than the 17-oxo group, reactive with organometallic compounds, with (2-R-ethynyl)magnesium halide or (2-R-ethynyl)lithium wherein R is hydrogen, methyl or trifluoromethyl.
- 2. A process according to claim 1 for preparing a compound of the formula ##STR3##where R is H, CH.sub.3 or CF.sub.3, which comprises treating a compound of the formula ##STR4##with a compound of the formula X-Mg-C.tbd.CR where X is chlorine, bromine or iodine, or with a compound of the formula LiC.tbd.CR, in an inert solvent under anhydrous conditions.
- 3. A process according to claim 2 wherein R is H.
- 4. A process for preparing 17.alpha.-pregn-4-en-20-yno[2,3-d]isoxazol-17-ol, according to claim 3, which comprises treating 17-oxoandrost-4-eno[2,3-d]isoxazole with ethynylmagnesium halide in an inert solvent under anhydrous conditions.
- 5. A process according to claim 4 wherein the ethynylmagnesium halide is ethynylmagnesium bromide.
- 6. A process for preparing 17.alpha.-pregn-4-en-20-yno[2,3-d]isoxazol-17-ol, according to claim 3, which comprises treating 17-oxoandrost-4-eno[2,3-d]isoxazole with monolithium acetylide in an inert solvent under anhydrous conditions.
- 7. A process for preparing 5.alpha.,17.alpha.-pregnan-20-yno[2,3-d]isoxazol-17-ol, according to claim 3, which comprises treating 17-oxo-5.alpha.-androstano[2,3-d]isoxazole with monolithium acetylide in an inert solvent under anhydrous conditions.
- 8. A process for preparing 4,4-dimethyl-17.alpha.-pregn-5-en-20-yno[2,3-d]isoxazol-17.beta.-ol, according to claim 1, which comprises treating 4,4-dimethylandrost-5-eno[2,3-d]isoxazol-17-one with ethynylmagnesium halide in an inert solvent under anhydrous conditions.
- 9. A process according to claim 2 wherein R is CF.sub.3.
- 10. A process for preparing 21-trifluoromethyl-17.alpha.-pregn-4-en-20-yno[2,3-d]isoxazol-17-ol, according to claim 9, which comprises treating 17-oxoandrost-4-eno[2,3-d]isoxazole with 3-trifluoro-1-propynylmagnesium halide in an inert solvent under anhydrous conditions.
- 11. 21-Trifluoromethyl-17.alpha.-pregn-4-en-20-yno[2,3-d]-isoxazol-17-ol.
Parent Case Info
This application is a continuation-in-part of application Ser. No. 619,579, filed Oct. 6, 1975, now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
3790564 |
Pierdet et al. |
Feb 1974 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
842,676 |
Jul 1960 |
UK |
Non-Patent Literature Citations (1)
Entry |
JACS, vol. 83 (1961) p. 4663-4664, by Fried et al. |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
619579 |
Oct 1975 |
|