Hydrochloric Acid → Nandrolone

HRID 1077210

Reaction equation

HRID 1077210 reaction equation
C[O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]1[OH:21].Cl.O>CO>[OH:21][C@H:12]1[CH2:11][CH2:10][C@H:9]2[C@H:8]3[C@H:17]([CH2:16][CH2:15][C@:13]12[CH3:14])[C@@H:18]1[C:5](=[CH:4][C:3](=[O:2])[CH2:20][CH2:19]1)[CH2:6][CH2:7]3

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 1019633-Methoxyestra-2,5(10)-dien-17beta-ol

Product 1

HCID 9904NandroloneYield 46.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve dl-3-methoxyestra-2,5(10)-dien-17β-ol (0.84 g) in methanol (18 ml) containing concentrated hydrochloric acid (1.2 ml) and water (0.8 ml) and allow the mixture to stand at room temperature for 15 hours. Add water and extract the mixture with ether. Wash, dry and evaporate the ethanol solution and dissolve the residue in a little benzene. Filter through a column of alumina (25 g) with benzene-ether (7.3). Evaporate the eluates and recrystallize the residue from ether-hexane to obtain the title compound (372 mg), m.p. 123°-124.5° or in an alternate form, m.p. 131°-132°; ultraviolet absorption maximum at 241 mμ (ε16,600); infrared absorption peaks at 6μ, 7.9 μ, 9.4 μ.

Workup

  1. extractionAdd water and extract the mixture with ether
  2. washWash
  3. customdry
  4. customevaporate the ethanol solution
  5. dissolutiondissolve the residue in a little benzene
  6. filtrationFilter through a column of alumina (25 g) with benzene-ether (7.3)
  7. customEvaporate the eluates
  8. customrecrystallize the residue from ether-hexane

Sources & evidence

ORD record
ord-6d227c4992e34cdaabde2effe41bc478
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Linked notes

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