Sodium Bicarbonate → HCID 13505217、化合物

HRID 1731750ノート

反応式

HRID 1731750 の反応式
[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]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 12429743But-1-ene-1,1-diolHCID 13371549HCID 13371549、化合物

生成物 1

HCID 13505217HCID 13505217、化合物収率 27.2%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9cc3ddac91e2460aac35edfb49ef9e2c
出典データセット
uspto-grants-1986_11
特許番号
US04623649

反応ノート

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