Cyclopropanecarbonyl chloride → HCID 18328985, compound
Reaction equation
[CH3:1][C:2]1[NH:16][CH2:15][CH2:14][C:4]2=[C:5]3[C:10](=[N:11][C:3]=12)[CH:9]=[CH:8][C:7]([O:12][CH3:13])=[CH:6]3.[CH:17]1([C:20](Cl)=[O:21])[CH2:19][CH2:18]1>ClCCl>[CH2:1]=[C:2]1[C:3]2[NH:11][C:10]3[C:5](=[CH:6][C:7]([O:12][CH3:13])=[CH:8][CH:9]=3)[C:4]=2[CH2:14][CH2:15][N:16]1[C:20]([CH:17]1[CH2:19][CH2:18]1)=[O:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 10-methoxyharmalan in anhydrous dichloromethane is added cyclopropylcarbonyl chloride. The solution becomes clear and is left to stir for 1 h at 0° C. After evaporation of the dichloromethane, the 1-methylene-2-cyclopropylcarbonyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline is recovered by chromatography on silica (pet. ether/EtOAc; 50/50). (The product turns yellow in the light).