Hydrogen Peroxide → 7alpha-Methyl-5-androstene-3alpha,17beta,19-triol

HRID 1390773Notes

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]([CH2:26][C:27](=[O:36])[CH2:28][CH2:29]1)=[CH:24][C@H:23]3[CH3:37].[OH-].[Na+].OO.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:37][C@@H:23]1[CH:24]=[C:25]2[C@:30]([CH2:31][OH:32])([CH2:29][CH2:28][C@@H:27]([OH:36])[CH2:26]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

An 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-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 stirred for an additional two hours. The reaction mixture is decomposed by the addition of a 3 N sodium hydroxide solution 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-5-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-a51d92cda229479e96bc635ac367ccfb
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04139617

Reaction notes

Loading…