Methanol → Exemestane

HRID 2065998

반응식

HRID 2065998 반응식
[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.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.CO.CC(OC)(C)C>CN1CCCC1>[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

참가 물질

6

반응물 4

HCID 887MethanolHCID 8371ChloranilHCID 15413tert-Butyl methyl etherHCID 129518006-Methylideneandrost-4-ene-3,17-dione

생성물 1

HCID 60198Exemestane수율 60.4%

시약·촉매·용매 1

HCID 84541-Methylpyrrolidine용매

반응 조건

온도
77.5 °C

실험 절차

6-Methylen-androst-4-ene-3,17-dione (5.0 gm) was dissolved in N-methylpyrrolidine (25 mL) at RT & to it was charged Chloranil (12.37 gm) at RT. The reaction mass was heated to 75 to 80° C. for 18 hours. The progress of the reaction is monitored on TLC. The reaction mass was cooled down to room temperature and methanol was added to it. The reaction mass was stirred for next 30 minutes and precipitated solid mass was filtered through buchner funnel and washed with methanol. All the filtrates were combined and suitably diluted. The product from aqueous solution was extracted in toluene. Combined toluene extracts was washed with 2% aqueous NaOH solution under stirring for 30 minutes. The toluene layer was separated and washed with water. Toluene layer was dried over sodium sulfate, filtered and evaporated at reduced pressure to get solid residue. The solid residue was treated with MTBE to get 3.0 gm solid product. HPLC Purity: 97%.

후처리

  1. temperatureThe reaction mass was cooled down to room temperature
  2. customprecipitated solid mass
  3. filtrationwas filtered through buchner funnel
  4. washwashed with methanol
  5. additionsuitably diluted
  6. extractionThe product from aqueous solution was extracted in toluene
  7. washCombined toluene extracts was washed with 2% aqueous NaOH solution
  8. stirringunder stirring for 30 minutes
  9. customThe toluene layer was separated
  10. washwashed with water
  11. dry with materialToluene layer was dried over sodium sulfate
  12. filtrationfiltered
  13. customevaporated at reduced pressure
  14. customto get solid residue

출처 및 근거

ORD 기록
ord-8871462b30404e98ae28401dc193bab5
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288571B2

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