Pentane → 6-Tert-butyl-4-methyl-beta-carboline-3-carboxylic acid ethyl ester

HRID 1731748Notes

Reaction equation

HRID 1731748 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH2:5]([O:7][C:8]([C:10]1[N:11]=[CH:12][C:13]2[NH:14][C:15]3[C:20]([C:21]=2[C:22]=1[CH3:23])=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:9])[CH3:6].CCCCC.[C:29](Cl)([CH3:32])([CH3:31])[CH3:30]>>[CH2:5]([O:7][C:8]([C:10]1[N:11]=[CH:12][C:13]2[NH:14][C:15]3[C:20]([C:21]=2[C:22]=1[CH3:23])=[CH:19][C:18]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:17][CH:16]=3)=[O:9])[CH3:6]

Participants

5

Reactant 4

HCID 8003PentaneHCID 10486tert-BUTYL CHLORIDEHCID 6451240Aluminum(III) ChlorideHCID 12795657HCID 12795657, compound

Product 1

HCID 135052146-Tert-butyl-4-methyl-beta-carboline-3-carboxylic acid ethyl ester

Procedure

1.2 g of aluminum trichloride is added to a suspension of 500 mg of 4-methyl-β-carboline-3-carboxylic acid ethyl ester in 15 ml of tert-butyl chloride. The mixture is stirred for 2 hours at room temperature and thereafter combined with 50 ml of pentane. The supernatant solution is removed by decanting, and the precipitate is combined with 10 ml of ethanol and 30 ml of water. After setting the pH at 3, the mixture is extracted repeatedly with ether. The collected organic phases are dried, filtered, and concentrated. Recrystallization from ether yields 250 mg of 6-tert-butyl-4-methyl-β-carboline-3-carboxylic acid ethyl ester, mp 201°-203° C. From the mother liquor, 100 mg of 6,8-di-tert-butyl-4-methyl-β-carboline-3-carboxylic acid ethyl ester can be isolated, mp 260°-263° C.

Workup

  1. customThe supernatant solution is removed
  2. customby decanting
  3. extractionthe mixture is extracted repeatedly with ether
  4. customThe collected organic phases are dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customRecrystallization from ether

Sources & evidence

ORD record
ord-5ba2adbe54394f16bb2d74ce5c9056ff
Source dataset
uspto-grants-1986_11
Patent number
US04623649

Reaction notes

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