Ethyl chloroformate → ethyl 2-acetyl-6-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-9-carboxylate

HRID 1004062Notes

Reaction equation

HRID 1004062 reaction equation
[OH-].[Na+].Cl[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19]1[CH:18]([CH3:24])[N:17]([C:25](=[O:27])[CH3:26])[CH2:16][CH2:15][C:14]2=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:25]([N:17]1[CH2:16][CH2:15][C:14]2[C:13]3[C:21](=[CH:22][CH:23]=[C:11]([O:10][CH3:9])[CH:12]=3)[N:20]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:19]=2[CH:18]1[CH3:24])(=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 18328986HCID 18328986, compound

Product 1

HCID 18794216ethyl 2-acetyl-6-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-9-carboxylateYield 70%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Sodium hydroxide (3 g), tetrabutylammonium hydrogen sulphate (1.87 g) and ethyl chloroformate (2.2 mL) are successively added to a solution of 1-(6-methoxy- 1-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-2-yl)-1-ethanone (1.45 g) in dichloromethane (100 mL). The mixture is stirred at room temperature for 3 h. After separation on silica gel (chloroform/methanol eluent), the ethyl 2-acetyl-6-methoxy-1 -methyl-2,3,4,9-tetrahydro-1H-β-carboline-9-carboxylate is obtained (70% yield).

Workup

  1. customAfter separation on silica gel (chloroform/methanol eluent)

Sources & evidence

ORD record
ord-0e949290e988481d916e0685d660a6f3
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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