Hydrogen Peroxide → 7alpha-Methyl-4-androstene-3alpha,17beta,19-triol

HRID 371835Notes

Reaction equation

C([BH-](C(CC)C)C(CC)C)(CC)C.[K+].[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](=[CH:26][C:27](=[O:36])[CH2:28][CH2:29]1)[CH2:24][C@H:23]3[CH3:37].[OH-].[Na+].OO.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:37][C@@H:23]1[CH2:24][C:25]2[C@:30]([CH2:31][OH:32])([CH2:29][CH2:28][C@@H:27]([OH:36])[CH:26]=2)[C@@H:33]2[C@@H:22]1[C@H:19]1[C@@:17]([CH2:35][CH2:34]2)([CH3:18])[C@@H:16]([OH:15])[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 0 °C

Procedure

A 0.5 M solution of potassium tri-sec-butylborohydride in tetrahydrofuran under nitrogen is cooled to -78° C. in a dry ice-acetone bath. 17β,19-Dihydroxy-7α-methyl-4-androsten-3-one in tetrahydrofuran is added slowly and the reaction mixture is stirred for a period of 2 hours at this temperature, warmed to 0° C., and stirred for an additional two hours. The reaction mixture is decomposed by the addition of 3 N sodium hydroxide followed by a 30% hydrogen peroxide solution. Solid potassium carbonate is added and the tetrahydrofuran solution decanted. The solid residue is washed with fresh tetrahydrofuran and the combined tetrahydrofuran solutions are dried over anhydrous sodium sulfate, filtered and the filtrate removed by evaporation. The residue is crystallized from acetone to yield 7α-methyl-4-androstene-3α,17β,19-triol.

Workup

stirringstirred 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
customthe filtrate removed by evaporation
customThe residue is crystallized from acetone

Sources & evidence

ORD record: ord-9ae0561c0cd14b288ff292e288b7e7ee
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04087524

Reaction notes

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