Sodium Bicarbonate → HCID 13505217, 화합물

HRID 1731750노트

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HRID 1731750 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14](I)=[CH:13][CH:12]=3)=[O:5])[CH3:2].C(=O)(O)[O-].[Na+].[C:26]([OH:31])([OH:30])=[CH:27][CH2:28][CH3:29]>CN1CCCC1=O.[Pd](Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([CH:28]1[CH2:29][O:30][CH:26]([OH:31])[CH2:27]1)=[CH:13][CH:12]=3)=[O:5])[CH3:2]

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 12429743But-1-ene-1,1-diolHCID 13371549HCID 13371549, 화합물

생성물 1

HCID 13505217HCID 13505217, 화합물수율 27.2%

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

Under argon, 720 mg (2 mmol) of 6-iodo-4-methyl-β-carboline-3-carboxylic acid ethyl ester is heated in a pressure vessel with 202 mg (2.4 mmol) of sodium bicarbonate, 75 mg (0.42 mmol) of palladium dichloride, and 705 mg (8 mmol) of butenediol in 10 ml of N-methylpyrrolidone for 2 hours to 150° C. After filtration and concentration, the mixture is distributed in ethyl acetate/water. The aqueous phase is extracted twice with ethyl acetate, the combined organic phases are dried, filtered, and concentrated. The residue is chromatographed over silica gel with toluene:ethanol=80:40 as the eluent. Recrystallization of the corresponding fractions from ethyl acetate/diisopropyl ether yields 185 mg (26% of theory) of 6-(2-hydroxytetrahydrofuran-4-yl)-4-methyl-β-carboline-3-carboxylic acid ethyl ester, mp 177°-180° C.

후처리

  1. filtrationAfter filtration and concentration
  2. extractionThe aqueous phase is extracted twice with ethyl acetate
  3. customthe combined organic phases are dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed over silica gel with toluene
  7. customRecrystallization of the corresponding fractions from ethyl acetate/diisopropyl ether

출처 및 근거

ORD 기록
ord-9cc3ddac91e2460aac35edfb49ef9e2c
출처 데이터셋
uspto-grants-1986_11
특허 번호
US04623649

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