Sodium Bicarbonate → HCID 13505217, compound

HRID 1731750Notes

Reaction equation

HRID 1731750 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 13505217HCID 13505217, compoundYield 27.2%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9cc3ddac91e2460aac35edfb49ef9e2c
Source dataset
uspto-grants-1986_11
Patent number
US04623649

Reaction notes

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