Ammonia → Nandrolone

HRID 2072268Notes

Reaction equation

HRID 2072268 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:18]2[C:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH:16]=3)([CH3:14])[C@@H:12]([O:21]C(C)(C)C)[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.NC1C=CC=CC=1.N.Cl([O-])(=O)(=O)=O.[Li+].Cl>C(O)C.[Hg].O>[CH3:14][C@@:13]12[C@@H:12]([OH:21])[CH2:11][CH2:10][C@H:9]1[C@@H:8]1[CH2:7][CH2:6][C:5]3[C@@H:18]([C@H:17]1[CH2:16][CH2:15]2)[CH2:19][CH2:20][C:3](=[O:2])[CH:4]=3

Participants

9

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 6115AnilineHCID 15097970HCID 15097970, compoundHCID 23665649Lithium perchlorate

Product 1

HCID 9904Nandrolone

Reagents, catalysts & solvents 3

HCID 23931MercuryCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

1.0 g. of 3-methoxy-17β-tert.-butoxy-1,3,5(10),9(11)-estratetraene is dissolved in 4 ml. of aniline and 3 ml of ethanol, added to 150 ml. of liquid ammonia, 5 g. of lithium perchlorate and electrolyzed for 2 hours at 1 ampere on a mercury electrode in a cell divided by a porous glass plate. After the mixture has been worked up, the crude product (1.1 g.) is dissolved in ethanol and heated with 3 ml. of concentrated hydrochloric acid. By gently adding water, 0.6 g. of nortestosterone is obtained after cooling which, after recrystallization from isopropyl ether, has a melting point of 108°-110° C.

Workup

  1. temperatureheated with 3 ml

Sources & evidence

ORD record
ord-08f20dc005b14b9e93bdaa719a80ee73
Source dataset
uspto-grants-1977_09
Patent number
US04050998

Reaction notes

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