tert-Butyl hydroperoxide → 3beta-Tribenzylsilyloxy-5,6beta-epoxy-7beta-hydroxy-15beta,16beta-methylene-5beta-androstan-17-one

HRID 1649470Notes

Reaction equation

[CH2:1]([Si:8]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[O:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C:12](=[CH:13][C@H:14]([OH:31])[C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[C@@H:17]3[CH2:30][C@@H:18]3[C:19]2=[O:29])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:50]O)(C)(C)C>C1(C)C=CC=CC=1>[CH2:39]([Si:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[O:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@:12]3([O:50][C@@H:13]3[C@H:14]([OH:31])[C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[C@@H:17]3[CH2:30][C@@H:18]3[C:19]2=[O:29])[CH2:11]1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

Conditions

Temperature: 80 °C

Procedure

24 g of 3β-tribenzylsilyloxy-7β-hydroxy-15β,16β-methylene-5-androsten-17-one is dissolved in 50 ml of toluene, combined with 500 mg of vanadium(IV) oxide acetylacetonate, and heated to 80° C. A solution of 75 ml tert.-butyl hydroperoxide (10 ml 80% tert.-butyl hydroperoxide in 100 ml of toluene) is added dropwise to the reaction mixture, and the latter is allowed to stand for 1.5 hours at this temperature. After cooling, the mixture is washed with water and saturated sodium chloride solution, dried, and evaporated under vacuum, thus obtaining 24.5 g of 3β-tribenzylsilyloxy-5,6β-epoxy-7β-hydroxy-15β,16β-methylene-5β-androstan-17-one.

Workup

temperatureAfter cooling
washthe mixture is washed with water and saturated sodium chloride solution
customdried
customevaporated under vacuum

Sources & evidence

ORD record: ord-3d9fd46dc7744f52b5e67ef5faa612c5
Source dataset: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04416985

Reaction notes

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