Cyclopropanecarbonyl chloride → HCID 18328985, compound

HRID 1004048Notes

Reaction equation

HRID 1004048 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

HCID 77637Cyclopropanecarbonyl chlorideHCID 178487038HCID 178487038, compound

Product 1

HCID 18328985HCID 18328985, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. waitis left
  2. customAfter evaporation of the dichloromethane
  3. customthe 1-methylene-2-cyclopropylcarbonyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline is recovered by chromatography on silica (pet. ether/EtOAc; 50/50)

Sources & evidence

ORD record
ord-f93dfc5dedba4102b07cbcb1751ee5b7
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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