Selective borane reductions of progesterone
Abstract
A number of selective reductions using borane end metal borohydrides has been described. In our studies of hydroboration of steroid conjugated ketones under different conditions and with different solvents we have found that borane reduces in a good yield the carbonyl group in C-3 of progesterone, without affecting the carbonyl in C-20, as well as the Delta4 double bound, thus giving as the main product, 3beta-hydroxy- 20-keto-Delta4-pregnene, which was obtained in a pure state by direct crystallization of the reaction product from methanol.
Keywords:
borane / progesterone / boric acid / oxidation reduction reactionSource:
Tetrahedron Letters, 1967, 8, 19, 1777-1779Publisher:
- Elsevier
DOI: 10.1016/S0040-4039(00)90721-4
ISSN: 0040-4039
PubMed: 6047532
Scopus: 2-s2.0-0014086295
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Institution/Community
IHTMTY - JOUR AU - Stefanović, Milutin AU - Lajšić, Stevan D. PY - 1967 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4661 AB - A number of selective reductions using borane end metal borohydrides has been described. In our studies of hydroboration of steroid conjugated ketones under different conditions and with different solvents we have found that borane reduces in a good yield the carbonyl group in C-3 of progesterone, without affecting the carbonyl in C-20, as well as the Delta4 double bound, thus giving as the main product, 3beta-hydroxy- 20-keto-Delta4-pregnene, which was obtained in a pure state by direct crystallization of the reaction product from methanol. PB - Elsevier T2 - Tetrahedron Letters T1 - Selective borane reductions of progesterone VL - 8 IS - 19 SP - 1777 EP - 1779 DO - 10.1016/S0040-4039(00)90721-4 ER -
@article{ author = "Stefanović, Milutin and Lajšić, Stevan D.", year = "1967", abstract = "A number of selective reductions using borane end metal borohydrides has been described. In our studies of hydroboration of steroid conjugated ketones under different conditions and with different solvents we have found that borane reduces in a good yield the carbonyl group in C-3 of progesterone, without affecting the carbonyl in C-20, as well as the Delta4 double bound, thus giving as the main product, 3beta-hydroxy- 20-keto-Delta4-pregnene, which was obtained in a pure state by direct crystallization of the reaction product from methanol.", publisher = "Elsevier", journal = "Tetrahedron Letters", title = "Selective borane reductions of progesterone", volume = "8", number = "19", pages = "1777-1779", doi = "10.1016/S0040-4039(00)90721-4" }
Stefanović, M.,& Lajšić, S. D.. (1967). Selective borane reductions of progesterone. in Tetrahedron Letters Elsevier., 8(19), 1777-1779. https://doi.org/10.1016/S0040-4039(00)90721-4
Stefanović M, Lajšić SD. Selective borane reductions of progesterone. in Tetrahedron Letters. 1967;8(19):1777-1779. doi:10.1016/S0040-4039(00)90721-4 .
Stefanović, Milutin, Lajšić, Stevan D., "Selective borane reductions of progesterone" in Tetrahedron Letters, 8, no. 19 (1967):1777-1779, https://doi.org/10.1016/S0040-4039(00)90721-4 . .