Sodium → HCID 12796469, compound

HRID 2049479Notes

Reaction equation

HRID 2049479 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]32OCC[O:26]3)[CH2:7][C@@H:6]1[OH:30])[CH3:3]>C(O)CC>[NH2:24][C@@H:19]1[CH2:18][C@@:16]2([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]2=[O: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:30])[C@@H:5]([O:4][CH2:2][CH3:3])[CH2:22]1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 88776434HCID 88776434, compound

Product 1

HCID 12796469HCID 12796469, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

Sodium (7.5 g) was added portionwise to a refluxing solution of 2β-ethoxy-17,17-ethylenedioxy-3α-hydroxy-5α-androstan-11-one 11-oxime (5.7 g) in propanol (400 ml) under nitrogen. Most of the solvent was evaporated in vacuo, water was added and the precipitated material was extracted into ethyl acetate. The washed extract was evaporated in vacuo and the residue was partitioned between ether and 2 N-hydrochloric acid. The aqueous layer was basified, extracted into ethyl acetate, washed, dried (Na2SO4) and evaporated to afford a froth which crystallized from ether to give the title compound m.p. 144°-148°, [α]D +61.5°.

Workup

  1. customMost of the solvent was evaporated in vacuo, water
  2. additionwas added
  3. extractionthe precipitated material was extracted into ethyl acetate
  4. extractionThe washed extract
  5. customwas evaporated in vacuo
  6. customthe residue was partitioned between ether and 2 N-hydrochloric acid
  7. extractionextracted into ethyl acetate
  8. washwashed
  9. dry with materialdried (Na2SO4)
  10. customevaporated
  11. customto afford a froth which
  12. customcrystallized from ether

Sources & evidence

ORD record
ord-bb5c2347870e40bc9019cf34ac322e5b
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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