Hydrogen Peroxide → 5-Androstene-3alpha,17beta,19-triol

HRID 1390771Notes

Reaction equation

C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[OH:15][C@H:16]1[CH2:21][CH2:20][C@H:19]2[C@H:22]3[C@H:33]([CH2:34][CH2:35][C@:17]12[CH3:18])[C@:30]1([CH2:31][OH:32])[C:25]([CH2:26][C:27](=[O:36])[CH2:28][CH2:29]1)=[CH:24][CH2:23]3.[OH-].[Na+].OO.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:18][C@:17]12[CH2:35][CH2:34][C@H:33]3[C@@H:22]([CH2:23][CH:24]=[C:25]4[C@:30]3([CH2:31][OH:32])[CH2:29][CH2:28][C@@H:27]([OH:36])[CH2:26]4)[C@@H:19]1[CH2:20][CH2:21][C@@H:16]2[OH:15]

Participants

Conditions

Temperature: 0 °C

Procedure

A 1 M solution of lithium tri-sec-butylborohydride in tetrahydrofuran under nitrogen is cooled in a dry ice-acetone bath to about -78° C. and 17β,19-dihydroxy-5-androsten-3-one in tetrahydrofuran is slowly added. The reaction mixture is stirred for a period of two hours at this temperature, warmed to 0° C. and stirring continued for an additional two hours. The reaction mixture is decomposed by the addition of a 3 N sodium hydroxide solution followed by the addition of a 30% hydrogen peroxide solution. Solid potassium carbonate is added and the tetrahydrofuran solution decanted therefrom. The solid residue is washed with fresh tetrahydrofuran and the combined tetrahydrofuran solutions are dried over anhydrous sodium sulfate, filtered, and evaporated. The residue is crystallized from acetone to yield 5-androstene-3α,17β,19-triol.

Workup

stirringstirring
waitcontinued for an additional two hours
customthe tetrahydrofuran solution decanted
washThe solid residue is washed with fresh tetrahydrofuran
dry with materialthe combined tetrahydrofuran solutions are dried over anhydrous sodium sulfate
filtrationfiltered
customevaporated
customThe residue is crystallized from acetone

Sources & evidence

ORD record: ord-7b45c6c2e839472bb649530c095ab18a
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04139617

Reaction notes

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