Dichloromethane → N-Ethylcarbamate 5-hydroxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Reaktionsgleichung

B(Br)(Br)Br.C(Cl)Cl.[CH2:8]([NH:10][C:11](=[O:13])[O-:12])[CH3:9].C[O:15][C:16]1[CH:17]=[CH:18][C:19]2[CH:20]([CH3:28])[CH:21]3[CH2:25][NH:24][CH2:23][CH:22]3[C:26]=2[CH:27]=1>>[CH2:8]([NH:10][C:11](=[O:12])[O-:13])[CH3:9].[OH:15][C:16]1[CH:17]=[CH:18][C:19]2[CH:20]([CH3:28])[CH:21]3[CH2:25][NH:24][CH2:23][CH:22]3[C:26]=2[CH:27]=1

Komponenten

Edukt 3

HCID 6344Dichloromethane

HCID 25134Boron tribromide

HCID 86602843N-Ethylcarbamate 5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Produkt 1

HCID 86602864N-Ethylcarbamate 5-hydroxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Versuchsvorschrift

BBr3 in CH2Cl2 (1.1 mL, 1.1 mmol, 1 M) was added to a solution of N-Ethylcarbamate-5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 2, Step A) (100 mg, 0.36 mmol) at 0° C. The reaction mixture was stirred overnight from 0° C. to room temperature and quenched with H2O. The solution was filtered through an Extrelut column, the column was washed with CH2Cl2, and the filtrate was concentrated. The crude product was obtained without further purification. MS calculated for C15H19NO3+H: 262, observed: 262.