Ammonia → 19-Hydroxy-5-androsten-17-one acetate

HRID 1390756Notes

Reaction equation

HRID 1390756 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].Cl[C@H:6]1[CH2:23][CH2:22][C@@:21]2([CH2:24][OH:25])[C:8](=[CH:9][CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C:15]2=[O:26])[CH2:7]1.[Li].N.C(O)C>O1CCCC1>[C:1]([OH:4])(=[O:3])[CH3:2].[OH:25][CH2:24][C@@:21]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:26])[CH2:14][CH2:13]4)[CH2:10][CH:9]=[C:8]1[CH2:7][CH2:6][CH2:23][CH2:22]2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 3028194LithiumHCID 867363153beta-Chloro-19-hydroxy-5-androsten-17-one acetate

Product 1

HCID 8673631419-Hydroxy-5-androsten-17-one acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3β-chloro-19-hydroxy-5-androsten-17-one acetate in anhydrous tetrahydrofuran is added with stirring to a solution of lithium in liquid ammonia. After approximately two hours of stirring, 95% ethanol is added via dropwise addition. The residue obtained after evaporation of the ammonia is treated with water and ether. The ether extract is washed with water, dried over magnesium sulfate and concentrated under vacuum. The residue which remains is crystallized from an acetone-hexane solution to yield 19-hyroxy-5-androsten-17-one acetate.

Workup

  1. customThe residue obtained
  2. customafter evaporation of the ammonia
  3. additionis treated with water and ether
  4. extractionThe ether extract
  5. washis washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue which remains is crystallized from an acetone-hexane solution

Sources & evidence

ORD record
ord-fc986ac0968c4146b934fcf15a11aac9
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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