Pyridine → HCID 12850022, compound

HRID 839592Notes

Reaction equation

HRID 839592 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]2.[C:23]12([C:33](Cl)=[O:34])[CH2:32][CH:27]3[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]3)[CH2:24]1)[CH2:30]2.N1C=CC=CC=1>C1(C)C=CC=CC=1>[C:23]12([C:33]([O:1][CH2:2][C@@:3]34[C@@H:20]5[C@H:11]([C@H:12]6[C@@:16]([CH2:18][CH2:19]5)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]6)[CH2:10][CH2:9][C:8]3=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]4)=[O:34])[CH2:30][CH:29]3[CH2:28][CH:27]([CH2:26][CH:25]([CH2:31]3)[CH2:24]1)[CH2:32]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 989151-Adamantanecarbonyl chlorideHCID 25237919-Hydroxyandrostenedione

Product 1

HCID 12850022HCID 12850022, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 22 g of 19-hydroxyandrost-4-ene-3,17-dione, 18 g of 1-adamantanecarboxylic acid chloride, and 29 ml of pyridine in 2.2 liters of toluene is refluxed overnight. The reaction mixture is cooled, and the toluene layer is washed with water, dried over magnesium sulfate and filtered then the solvent is removed. The resulting residue is crystallized from methanol to give 19-(1-adamantanylcarbonyloxy)androst-4-ene-3,17-dione, M.P. 161°-163° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. washthe toluene layer is washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent is removed
  6. customThe resulting residue is crystallized from methanol

Sources & evidence

ORD record
ord-f675412c3d7246d38a1bf3bbb298b912
Source dataset
uspto-grants-1978_06
Patent number
US04096254

Reaction notes

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