Sodium → HCID 12796503, compound

HRID 2049484Notes

Reaction equation

HRID 2049484 reaction equation
[CH2:1]1[CH2:26][O:25][C:3]2([CH2:8][CH2:7][C@H:6]3[C@H:9]4[C@H:19]([C:20](=[N:22]O)[CH2:21][C@:4]23[CH3:5])[C@:17]2([CH3:18])[C@H:12]([CH2:13][C@H:14]([OH:24])[CH2:15][CH2:16]2)[CH2:11][CH2:10]4)[O:2]1.[Na]>C(O)CC>[NH2:22][C@@H:20]1[CH2:21][C@@:4]2([CH3:5])[C@@H:6]([CH2:7][CH2:8][C:3]32[O:2][CH2:1][CH2:26][O:25]3)[C@H:9]2[C@H:19]1[C@:17]1([CH3:18])[C@@H:12]([CH2:11][CH2:10]2)[CH2:13][C@H:14]([OH:24])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 86736927HCID 86736927, compound

Product 1

HCID 12796503HCID 12796503, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A solution of 17,17-ethylenedioxy-11-oximino-5α-androstan-3α-ol (0.700 g) in propanol (20 ml) was refluxed under nitrogen. To this solution were added small pieces of sodium (total 0.8 g) over a period of 80 mins. The reaction mixture was evaporated to low volume then diluted with water. No precipitation occurred and the solution was partitioned between ethyl acetate and water. The ethyl acetate solution was washed with water (×4), dried (magnesium sulphate) and evaporated to a solid (0.575 g). Crystallisation from ethyl acetate/petrol gave colourless crystals of the title compound (0.396 g), m.p. 170°-171°, [α]D -36°.

Workup

  1. customThe reaction mixture was evaporated to low volume
  2. additionthen diluted with water
  3. customNo precipitation
  4. customthe solution was partitioned between ethyl acetate and water
  5. washThe ethyl acetate solution was washed with water (×4)
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated to a solid (0.575 g)
  8. customCrystallisation from ethyl acetate/petrol

Sources & evidence

ORD record
ord-13ce92ce685942c1a147f9123e6fd9bb
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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