Diethyl Ether → 3-Benzoyl-5-(2-chlorobenzyl)-4-methoxymethyl-beta-carboline

HRID 1720327Notes

Reaction equation

HRID 1720327 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[N:10](S(C3C=CC(C)=CC=3)(=O)=O)[C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29])[CH:14]=[CH:13][CH:12]=3)=O)C.[C:40]1([Li])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.CCOCC>O1CCCC1>[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[CH2:19][O:20][CH3:21])=[C:15]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29])[CH:14]=[CH:13][CH:12]=3)(=[O:3])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 539902425-(2-Chlorobenzyl)-4-methoxymethyl-9-tosyl-beta-carboline-3-carboxylic acid ethyl esterHCID 178506676HCID 178506676, compound

Product 1

HCID 98461173-Benzoyl-5-(2-chlorobenzyl)-4-methoxymethyl-beta-carbolineYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of 1.2 g (0.0021 mol) of 5-(2-chlorobenzyl)-4-methoxymethyl-9-tosyl-β-carboline-3-carboxylic acid ethyl ester in 60 ml of absolute tetrahydrofuran is slowly added 2.4 ml of a 2-molar solution of phenyllithium in bezene/ether at -70° C. under argon protection. The reaction mixture is stirred for another 15 minutes at -70° C. then for 3 hours at room temperature and finally for one hour at 35° C. The it is concentrated by evaporation. The residue is taken up in 150 ml of ethyl acetate. The solution in succession is washed with citric acid solution, water, sodium bicarbonate solution, water, saturated common salt solution and once more with water, dried and concentrated by evaporation. After chromatography on silica gel with equal parts of toluene and ethyl acetate and recrystallization from ethanol, 0.15 g (16% of theory) of 3-benzoyl-5-(2-chlorobenzyl)-4-methoxymethyl-β-carboline is obtained, melting point 147°-148° C.

Workup

  1. customat -70° C.
  2. waitfor 3 hours at room temperature
  3. waitfinally for one hour at 35° C
  4. concentrationThe it is concentrated by evaporation
  5. washThe solution in succession is washed with citric acid solution, water, sodium bicarbonate solution, water, saturated common salt solution and once more with water
  6. customdried
  7. concentrationconcentrated by evaporation
  8. customAfter chromatography on silica gel with equal parts of toluene and ethyl acetate and recrystallization from ethanol

Sources & evidence

ORD record
ord-80ccd3830e38431c8ede2a95e82763d8
Source dataset
uspto-grants-1996_04
Patent number
US05506234

Reaction notes

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