Reaction #93683

ord-84a0b588c67b42cf91f732ab7f5f1ccb

Reaction equation

C#C[C@]1(O)C(=C)C[C@H]2[C@@H]3C[C@@H](CN(CC)c4ccccc4)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C
17α-Ethynyl-17β-hydroxy-6-β-(N-phenyl-N-ethylaminomethyl)-16-methyleneandrosta-4-en-3-one
C#C[C@]1(O)C(=C)C[C@H]2[C@@H]3C[C@@H](CN(CC)c4ccccc4)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C
17α-Ethynyl-17β-hydroxy-6β-(N-phenyl-N-ethylaminomethyl)-16-methyleneandrosta-4-en-3-one
Cl
hydrochloric acid
O
Water
→
C#C[C@]1(O)C(=C)C[C@H]2[C@@H]3CC(=C)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C
title compound
C#C[C@]1(O)C(=C)C[C@H]2[C@@H]3CC(=C)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C
17α-Ethynyl-17β-hydroxy-6,16-dimethyleneandrosta-4-en-3-one

Reactants

C#C[C@]1(O)C(=C)C[C@H]2[C@@H]3C[C@@H](CN(CC)c4ccccc4)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C
17α-Ethynyl-17β-hydroxy-6-β-(N-phenyl-N-ethylaminomethyl)-16-methyleneandrosta-4-en-3-one
C#C[C@]1(O)C(=C)C[C@H]2[C@@H]3C[C@@H](CN(CC)c4ccccc4)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C
17α-Ethynyl-17β-hydroxy-6β-(N-phenyl-N-ethylaminomethyl)-16-methyleneandrosta-4-en-3-one
Cl
hydrochloric acid
O
Water

Reagents

None

Solvents

C1CCOC1
THF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

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

Procedure

17α-Ethynyl-17β-hydroxy-6-β-(N-phenyl-N-ethylaminomethyl)-16-methyleneandrosta-4-en-3-one (Example 3) 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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04614621uspto-grants-1986_09