Pyridine → HCID 12850022, compound

HRID 597360Notes

Reaction equation

HRID 597360 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-c9238ed8d9f4454398bd056a4afd6988
Source dataset
uspto-grants-1977_03
Patent number
US04013762

Reaction notes

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