Nandrolone → HCID 11760130, compound

HRID 1974426Notes

Reaction equation

HRID 1974426 reaction equation
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@H:20]([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3>C(OC(=O)C)(=O)C.C(Cl)(=O)C>[C:10]([O:17][C:16]1[CH2:18][CH2:19][C@H:20]2[C:14](=[CH:13][CH2:12][C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH2:8][CH2:9][C@@H:10]2[O:11][C:16](=[O:17])[CH3:15])[CH:15]=1)(=[O:11])[CH3:9]

Participants

4

Reactant 1

HCID 9904Nandrolone

Product 1

HCID 11760130HCID 11760130, compound

Reagents, catalysts & solvents 2

HCID 6367Acetyl chlorideSolventHCID 7918Acetic AnhydrideSolvent

Procedure

The compound 19-nortestosterone, 400 g, is refluxed under nitrogen in a mixture of 1500 ml of acetic anhydride and 1500 ml of acetyl chloride for a period of 3 hours. The volatile solvents are distilled at atmospheric pressure and the final traces of solvent removed under reduced pressure. The solid residue which remains is triturated with ice water, filtered, washed with cold aqueous sodium bicarbonate solution, rinsed with water and dried. Two recrystallizations of this residue from acetone yield 370 g of 3,17β-diacetoxyestr-3,5-diene which melts at 165°-71° C.

Workup

  1. distillationThe volatile solvents are distilled at atmospheric pressure
  2. customthe final traces of solvent removed under reduced pressure
  3. customThe solid residue which remains is triturated with ice water
  4. filtrationfiltered
  5. washwashed with cold aqueous sodium bicarbonate solution
  6. washrinsed with water
  7. customdried
  8. customTwo recrystallizations of this residue from acetone yield 370 g of 3,17β-diacetoxyestr-3,5-diene which melts at 165°-71° C.

Sources & evidence

ORD record
ord-fa609a1f85454bc6a481a1e363ed4025
Source dataset
uspto-grants-1976_12
Patent number
US04000273

Reaction notes

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