Fluorine → Meconin

HRID 336813

반응식

HRID 336813 반응식
CN1[C@@H]([C@H:12]2[O:21][C:19](=[O:20])[C:18]3[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=[CH:14][C:13]2=3)C2C(OC)=C3OCOC3=CC=2CC1.[F-].FF>C1COCC1>[CH3:25][O:24][C:16]1[C:17]([O:22][CH3:23])=[C:18]2[C:13]([CH2:12][O:21][C:19]2=[O:20])=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 24524FluorineHCID 28179Fluoride IonHCID 275196Noscapine

생성물 1

HCID 68437Meconin수율 74%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Aromatic fluorination of noscapine was achieved by employing the fluoride form of Amberlyst-A 26, a macroreticular anion-exchange resin containing quaternary ammonium groups. The method described [33] for Hal/F exchange may also be applied to other Hal/Hal′ exchange reactions. In Br/F exchange reactions, good yields were obtained only when a large molar ratio of the resin with respect to the substrate was employed. Thus, after refluxing a solution of bromonoscapine in anhydrous THF and an excess of Amberlyst-A 26 (fluorine, polymer-supported, 10 milliequivalents of dry resin; the average capacity of the resin is 4 milliequivalents per gram) for 12 hours, the resin was filtered off and the solvent was removed in vacuo to afford the desired compound (3) in 74% yield. The resin was recovered by washing with 1 N NaOH and then rinsing thoroughly with water until neutrality to generate the hydroxy-form of the resin. It was then stirred overnight with 1 N aqueous hydrofluoric acid, washed with acetone, ether and dried in a vacuum oven at 50° C. for 12 hours to afford the regenerated Amberlyst-A 26 (fluorine, polymer-supported), which can be reused.

후처리

  1. additiona macroreticular anion-exchange resin containing quaternary ammonium groups
  2. customIn Br/F exchange reactions, good yields
  3. customwere obtained only when a large molar ratio of the resin with respect to the substrate
  4. customfor 12 hours
  5. filtrationthe resin was filtered off
  6. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-6a98af94e77f4eb38471afa6e3153f02
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889705B2

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