Reacción #595398

Ecuación de reacción

LiBr

m-anisidine

ethyl 8-Methyl-5-(oxiran-2-ylmethyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

→

desired product

Rendimiento 67.2%

Ethyl 5-(2-Hydroxy-3-(3-methoxyphenylamino)propyl)-8-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Rendimiento 67.2%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroUpon completion the reaction was partitioned between EtOAc/H2O
2. 2
   Concentraciónthe organic layer was concentrated to an orange oil
3. 3
   OtroThe crude residue was purified by chromatography (SiO2, 0-50% EtOAc/Hexane)

Procedimiento

Following a literature procedure (Chakraborti et al., Eur. J. Org. Chem. 2004, 3597-3600) LiBr (0.001 g, 0.010 mmol) and m-anisidine (0.011 mL, 0.102 mmol) were added to ethyl 8-Methyl-5-(oxiran-2-ylmethyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (0.032 g, 0.102 mmol) and stirred vigorously at ambient temperature overnight. Upon completion the reaction was partitioned between EtOAc/H2O, and the organic layer was concentrated to an orange oil. The crude residue was purified by chromatography (SiO2, 0-50% EtOAc/Hexane) to afford the desired product (30 mg, 67%).

Fuente