Sodium → HCID 12796465, compound

HRID 2049476Notes

Reaction equation

HRID 2049476 reaction equation
[Na].[CH2:2]([O:4][C@H:5]1[CH2:22][C@@:21]2([CH3:23])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:20]2[C:19](=[N:24]O)[CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C:15]2=[CH2:26])[CH2:7][C@@H:6]1[OH:27])[CH3:3]>C(O)CC.O>[NH2:24][C@@H:19]1[CH2:18][C@@:16]2([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]2=[CH2:26])[C@H:11]2[C@H:20]1[C@:21]1([CH3:23])[C@@H:8]([CH2:9][CH2:10]2)[CH2:7][C@H:6]([OH:27])[C@@H:5]([O:4][CH2:2][CH3:3])[CH2:22]1

Participants

5

Reactant 2

HCID 5360545SodiumHCID 86736926HCID 86736926, compound

Product 1

HCID 12796465HCID 12796465, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10311-PropanolSolvent

Procedure

Sodium (2.7 g) was added portionwise to a stirred and refluxing solution of 2β-ethoxy-3α-hydroxy-17-methylene-5α-androstan-11-one 11-oxime (1.7 g) in propanol (100 ml) under nitrogen. The cooled reaction mixture was diluted with water and the precipitated solid (1.43 g) was collected by filtration. A portion of this material (300 mg) was purified by partitioning between 2 N-hydrochloric acid and ether when the insoluble hydrochloride which precipitated was collected by filtration and again partitioned between ether and 2 N-sodium hydroxide solution. The organic layer was washed, dried (Na2SO4) and evaporated to give the title compound as a froth (180 mg), [α]D +1.6°.

Workup

  1. customThe cooled reaction mixture
  2. filtrationthe precipitated solid (1.43 g) was collected by filtration
  3. customA portion of this material (300 mg) was purified
  4. customby partitioning between 2 N-hydrochloric acid and ether when the insoluble hydrochloride which
  5. customprecipitated
  6. filtrationwas collected by filtration
  7. customagain partitioned between ether and 2 N-sodium hydroxide solution
  8. washThe organic layer was washed
  9. dry with materialdried (Na2SO4)
  10. customevaporated

Sources & evidence

ORD record
ord-a7ed3606cea445f399a80f16d25ef956
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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