Hydrochloric Acid → 17alpha-Ethynyl-17beta-hydroxy-6,16-dimethyleneandrosta-4-en-3-one

HRID 370416

Reaction equation

HRID 370416 reaction equation
[C:1]([C@:3]1([OH:34])[C:8](=[CH2:9])[CH2:7][C@H:6]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:4]12[CH3:5])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:23])[CH2:16][CH2:17]1)[C@H:12]([CH2:24]N(C1C=CC=CC=1)CC)[CH2:11]3)#[CH:2].Cl.O>C1COCC1>[C:1]([C@:3]1([OH:34])[C:8](=[CH2:9])[CH2:7][C@H:6]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:4]12[CH3:5])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:23])[CH2:16][CH2:17]1)[C:12](=[CH2:24])[CH2:11]3)#[CH:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 1331492617alpha-Ethynyl-17beta-hydroxy-6beta-(N-phenyl-N-ethylaminomethyl)-16-methyleneandrosta-4-en-3-one

Product 1

HCID 1331492917alpha-Ethynyl-17beta-hydroxy-6,16-dimethyleneandrosta-4-en-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17α-Ethynyl-17β-hydroxy-6β-(N-phenyl-N-ethylaminomethyl)-16-methyleneandrosta-4-en-3-one (Example 5) in THF (20 ml) are mixed. Degassed hydrochloric acid (6N, 55 ml plus 20 ml THF) are added. The mixture is stirred overnight at 20°-25° under nitrogen, at which time TLC shows the reaction to be complete. Water (110 ml) is added, the mixture filtered, the solids washed with 10% hydrochloric acid, twice with water, once with 5% sodium bicarbonate, and three times with water to neutrality. Solids were then dried under nitrogen overnight to give the title compound.

Workup

  1. customthe reaction
  2. filtrationthe mixture filtered
  3. washthe solids washed with 10% hydrochloric acid, twice with water, once with 5% sodium bicarbonate, and three times with water to neutrality
  4. customSolids were then dried under nitrogen overnight

Sources & evidence

ORD record
ord-4f9918abd77142c49503c4720ebaec35
Source dataset
uspto-grants-1985_07
Patent number
US04526720

Linked notes

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