Ethylenediamine → HCID 86740722, compound

HRID 1380491Notes

Reaction equation

HRID 1380491 reaction equation
[OH-].[K+].[CH2:3](N)[CH2:4]N.[CH3:7][O:8][C:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]2=[O:28])[CH:10]=1>C(O)(C)(C)C>[C:3]([C@@:18]1([OH:28])[CH2:17][CH2:16][C@H:15]2[C@H:14]3[C@H:23]([CH2:22][CH2:21][C@:19]12[CH3:20])[C@:24]1([CH3:27])[C:11]([CH:10]=[C:9]([O:8][CH3:7])[CH2:26][CH2:25]1)=[CH:12][CH2:13]3)#[CH:4]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 14797Potassium HydroxideHCID 926873-Methoxyandrosta-3,5-dien-17-one

Product 1

HCID 86740722HCID 86740722, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Potassium hydroxide (7.75 g), calcium carbide (21.0 g), t-butanol (19 ml) and ethylene diamine (187 ml) are combined in a 500 ml Parr pressure bottle which is sealed with a foil covered rubber stopper which is wired to the bottle. The heterogenous mixture is stirred at 40° for about 16 hr (though about 4 hr is sufficient). The mixture is cooled to 20°-25° and 3-methoxyandrosta-3,5-dien-17-one (IAa, 11.80 g) is added as a solid. The reaction mixture is then stirred at 20°-25° for 5 hr. The mixture is transferred to a flask with a mechanical stirrer. The mixture is washed with methylene chloride (300 ml), cooled to 0°, quenched under a nitrogen atmosphere by the slow addition of acetic acid (57.2 ml). Water (300 ml) is added at a sufficiently slow rate to keep foaming under control. The mixture is filtered and the solids washed with methylene chloride. The filtrate phases are separated, the aqueous phase is back-extracted (twice) with methylene chloride. The organic phases are combined, washed with water (three times), dried over sodium sulfate and concentrated to an oil. The oil in ethyl acetate (75 ml) is heated to reflux and is allowed to crystallize at 20°-25° overnight to give the title compound, NMR (CDCl3) 0.90, 1.0, 2.47, 3.59, 5.15 and 5.23 δ.

Workup

  1. customis sealed with a foil
  2. temperatureThe mixture is cooled to 20°-25°
  3. stirringThe reaction mixture is then stirred at 20°-25° for 5 hr
  4. customThe mixture is transferred to a flask with a mechanical stirrer
  5. washThe mixture is washed with methylene chloride (300 ml)
  6. temperaturecooled to 0°
  7. customquenched under a nitrogen atmosphere by the slow addition of acetic acid (57.2 ml)
  8. additionWater (300 ml) is added at a sufficiently slow rate
  9. filtrationThe mixture is filtered
  10. washthe solids washed with methylene chloride
  11. customThe filtrate phases are separated
  12. extractionthe aqueous phase is back-extracted (twice) with methylene chloride
  13. washwashed with water (three times)
  14. dry with materialdried over sodium sulfate
  15. concentrationconcentrated to an oil
  16. temperatureThe oil in ethyl acetate (75 ml) is heated
  17. temperatureto reflux
  18. customto crystallize at 20°-25° overnight

Sources & evidence

ORD record
ord-67e5ebdf989d48f1bd23dbe736a850f9
Source dataset
uspto-grants-1986_04
Patent number
US04582644

Reaction notes

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