19-Tetrahydropyranyloxy-4-androstene-3,17-dione → 19-Tetrahydropyranyloxy-5alpha-androstane-3,17-dione

HRID 1834986Notes

Reaction equation

HRID 1834986 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C@@:9]12[C@@H:26]3[C@H:17]([C@H:18]4[C@@:22]([CH2:24][CH2:25]3)([CH3:23])[C:21](=[O:27])[CH2:20][CH2:19]4)[CH2:16][CH2:15][C:14]1=[CH:13][C:12](=[O:28])[CH2:11][CH2:10]2.[CH3:29][Si:30]([CH3:54])([CH3:53])[O:31][CH2:32][C@@:33]12[C@@H:50]3[C@H:41]([C@H:42]4[C@@:46]([CH2:48][CH2:49]3)([CH3:47])[C:45](=[O:51])[CH2:44][CH2:43]4)[CH2:40][CH2:39][C:38]1=[CH:37][C:36](=[O:52])[CH2:35][CH2:34]2>>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C@@:9]12[C@@H:26]3[C@H:17]([C@H:18]4[C@@:22]([CH2:24][CH2:25]3)([CH3:23])[C:21](=[O:27])[CH2:20][CH2:19]4)[CH2:16][CH2:15][C@H:14]1[CH2:13][C:12](=[O:28])[CH2:11][CH2:10]2.[CH3:53][Si:30]([CH3:29])([CH3:54])[O:31][CH2:32][C@@:33]12[C@@H:50]3[C@H:41]([C@H:42]4[C@@:46]([CH2:48][CH2:49]3)([CH3:47])[C:45](=[O:51])[CH2:44][CH2:43]4)[CH2:40][CH2:39][C@H:38]1[CH2:37][C:36](=[O:52])[CH2:35][CH2:34]2

Participants

4

Reactant 2

HCID 1009156119-Tetrahydropyranyloxy-4-androstene-3,17-dioneHCID 2280149719-Trimethylsiloxy-4-androstene-3,17-dione

Product 2

HCID 2280152619-Tetrahydropyranyloxy-5alpha-androstane-3,17-dioneHCID 2280152719-Trimethylsiloxy-5alpha-androstane-3,17-dione

Procedure

Substituting 17β-hydroxy-4,6α,17α-trimethyl-4-androstene-3,19-dione, 17β-hydroxy-4,6α,17α-trimethyl-4-androstene-3,19-dione acetate, 19-tetrahydropyranyloxy-4-androstene-3,17-dione, 19-trimethylsiloxy-4-androstene-3,17-dione and 6α-methyl-19-(2'-tetrahydropyranyloxy)-4-androstene-3,17-dione for the 4,6α,17α-trimethyl-17β,19-di(2'-tetrahydropyranyloxy)-4-androsten-3-one above results in the preparation of 17β-hydroxy-4,6α,17α-trimethyl-5α-androstane-3,19-dione, 17β-hydroxy-4,6α,17α-trimethyl-5α-androstane-3,19-dione acetate, 19-tetrahydropyranyloxy-5α-androstane-3,17-dione, 19-trimethylsiloxy-5α-androstane-3,17-dione and 6α-methyl-19-(2'-tetrahydropyranyloxy)-5α-androstane-3,17-dione, respectively.

Sources & evidence

ORD record
ord-a0eba5d30e194821829d06106c589a9a
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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