Selenium Dioxide → Exemestane

HRID 1200169

Reaction equation

HRID 1200169 reaction equation
[CH2:1]=[C:2]1[C:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[CH2:3]1.[Se](=O)=O>C(O)(C)(C)C>[CH2:1]=[C:2]1[C:19]2[C@:14]([CH3:21])([CH:15]=[CH:16][C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[CH2:3]1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 129518006-Methylideneandrost-4-ene-3,17-dione

Product 1

HCID 60198ExemestaneYield 40.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 6-methylenandrost-4-ene-3,17-dione (0.50 g), selenium dioxide (0.50 g) and t-butylalcohol (200 ml) was heated to reflux under nitrogen for about 30 hours. The cooled solution was filtered and then evaporated to dryness under reduced pressure. The residue was taken up in ethyl acetate (100 ml), treated with charcoal and washed consecutively with water, ammonium sulfide solution, cold 17% ammonium hydroxide, cold dilute hydrochloric acid, water, dried with sodium sulfate and finally evaporated to dryness. The crude product was chromatographed as described in example 1 to yield 0.20 g of pure 6-methylenandrosta-1,4-diene-3,17-dione, m.p. 188°-191° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for about 30 hours
  3. filtrationThe cooled solution was filtered
  4. customevaporated to dryness under reduced pressure
  5. additiontreated with charcoal
  6. washwashed consecutively with water, ammonium sulfide solution, cold 17% ammonium hydroxide, cold dilute hydrochloric acid, water
  7. dry with materialdried with sodium sulfate
  8. customfinally evaporated to dryness
  9. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-90ef8924fd2e4f759fb0ef37bff637d9
Source dataset
uspto-grants-1990_02
Patent number
US04904650

Linked notes

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