Androstenedione → Dihydrotestosterone

HRID 1729964Notes

Reaction equation

HRID 1729964 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21].CN.[Cl-].[Li+]>[Pt].[C-]#[W].O1CCCC1>[CH3:16][C@@:15]12[C@H:17]3[CH2:18][CH2:19][C@:2]4([CH3:1])[C@@H:3]([OH:21])[CH2:4][CH2:5][C@H:6]4[C@@H:7]3[CH2:8][CH2:9][C@H:10]1[CH2:11][C:12](=[O:20])[CH2:13][CH2:14]2

Participants

7

Reactant 3

HCID 6128AndrostenedioneHCID 6329MethylamineHCID 433294Lithium Chloride

Product 1

HCID 10635Dihydrotestosterone

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 25504Tungsten carbideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.50 g. of androst-4-ene-3,17-dione is dissolved in 10 ml. of tetrahydrofuran and electrolyzed in 100 ml. of methylamine with 0.5 g. of lithium chloride for 1 hour between a platinum cathode and a tungsten carbide anode at 0.5 A. After the reaction mixture has been worked up and recrystallized, 0.38 g. of 5α-androstan-17β-ol-3-one is obtained, m.p. 172.5° - 173.5° C.

Workup

  1. customrecrystallized

Sources & evidence

ORD record
ord-76bc9c68416e46bd9f72c9b1f7bbf465
Source dataset
uspto-grants-1976_11
Patent number
US03990956

Reaction notes

Loading…