2-Pyrrolidone → Levcromakalim

HRID 1905780

반응식

HRID 1905780 반응식
C(C1C=CC2OC(C)(C)[C@@H](Br)[C@H](O)C=2C=1)#N.[H-].[Na+].[C:19]([C:21]1[CH:33]=[CH:32][C:24]2[O:25][C:26]([CH3:31])([CH3:30])[CH:27]3[O:29][CH:28]3[C:23]=2[CH:22]=1)#[N:20].[NH:34]1[CH2:38][CH2:37][CH2:36][C:35]1=[O:39]>CS(C)=O.O>[C:19]([C:21]1[CH:33]=[CH:32][C:24]2[O:25][C:26]([CH3:31])([CH3:30])[C@@H:27]([OH:29])[C@H:28]([N:34]3[CH2:38][CH2:37][CH2:36][C:35]3=[O:39])[C:23]=2[CH:22]=1)#[N:20]

참가 물질

7

반응물 4

HCID 120252-PyrrolidoneHCID 24758Sodium hydride2회HCID 6932483trans-2,2-Dimethyl-3-bromo-6-cyanochroman-4-olHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

생성물 1

HCID 93504Levcromakalim수율 60%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

A solution of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-bromo-4-hydroxy-2H-benzo[b]pyran (4 g, 14.2 mM) in dimethylsulphoxide (20 ml) was stirred and sodium hydride (60% dispersion in oil, 0.6 g, 15 mM) added. The suspension was stirred for 1 hour when a solution of 6-cyano-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-benzo[b]pyran resulted. 2-Pyrrolidone (1.8 g, 21 mM) and further sodium hydride (0.8 g, 21 mM) were introduced and the mixture stirred at room temperature for an additional 16 hours. Water (40 ml) was slowly added to the mixture to induce crystallisation of the product after which it was cooled in ice and filtered under suction. Crystallisation from ethanol (20 ml) gave the title compound as a cream coloured solid in 60% yield. Recrystallisation from ethyl acetate afforded the pure product as needles, m.p. 226.5°-227.5° having an nmr spectrum and t.l.c. characteristics identical to those of the compound of Description 6.

후처리

  1. customresulted
  2. customcrystallisation of the product after which it
  3. temperaturewas cooled in ice
  4. filtrationfiltered under suction
  5. customCrystallisation from ethanol (20 ml)

출처 및 근거

ORD 기록
ord-7280985195ea4d38820d82e3627e7466
출처 데이터셋
uspto-grants-1987_03
특허 번호
US04647670

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