Ammonia → Dihydrotestosterone

HRID 1729965Notes

Reaction equation

HRID 1729965 reaction equation
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C@H:14]3[CH2:20][C:18](=[O:19])[CH:17]=[CH:16][C@:15]3([CH3:21])[C@H:5]1[CH2:4][CH2:3]2.N.[Cl-].[Na+]>[Au].O1CCCC1>[CH3:21][C@@:15]12[C@H:5]3[CH2:4][CH2:3][C@:2]4([CH3:1])[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]4[C@@H:6]3[CH2:12][CH2:13][C@H:14]1[CH2:20][C:18](=[O:19])[CH2:17][CH2:16]2

Participants

6

Reactant 3

HCID 222AmmoniaHCID 5234Sodium ChlorideHCID 2366661-Testosterone

Product 1

HCID 10635Dihydrotestosterone

Reagents, catalysts & solvents 2

HCID 23985GoldCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.5 g. of 5α-androst-1-en-17β-ol-3-one in 20 ml. of tetrahydrofuran is reacted in 150 ml. of ammonia for 15 minutes at 0.2 A/cm2 in a divided cell with the use of sodium chloride as the conductive salt and a gold cathode and an anode of glass-like carbon. After the catholyte has been worked up and the crude product has been recrystallized, 0.38 g. of 5α-androstan-17β-ol-3-one is obtained, m.p. 173° - 175° C.

Workup

  1. customthe crude product has been recrystallized

Sources & evidence

ORD record
ord-afc7c7fbcd5243758a7eea67a8fc83b5
Source dataset
uspto-grants-1976_11
Patent number
US03990956

Reaction notes

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