Acetic Anhydride → HCID 15816962, compound

HRID 1004047Notes

Reaction equation

HRID 1004047 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.[C:17](OC(=O)C)(=[O:19])[CH3:18].C(OCC)(=O)C>N1C=CC=CC=1>[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:17](=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 178487038HCID 178487038, compound

Product 1

HCID 15816962HCID 15816962, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 10-methoxyharmalan (1 mmol) in pyridine (2 ml) is added acetic anhydride (1.1 eq) . After acid hydrolysis and extraction with ethyl acetate, the crude product is flash-chromatographed (eluent: EtOAc/pet. ether; 50/50). The 1-methylene-2-acetyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline elutes off first.

Workup

  1. customthe crude product is flash-chromatographed (eluent: EtOAc/pet. ether; 50/50)

Sources & evidence

ORD record
ord-895b5cbf72bf41449642c4b4c5758390
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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