Reacción #595416

Ecuación de reacción

tert-butyl 8-bromo-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

potassium hydroxide

2-(phenoxymethyl)oxirane

→

tert-butyl 8-bromo-5-(2-hydroxy-3-phenoxypropyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Rendimiento 21.0%

Disolventes

acetone

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrocondensed
2. 2
   Lavadowashed twice with water
3. 3
   SecadoThe organic layer was then dried over Na2SO4
4. 4
   Filtraciónfiltered
5. 5
   Otrocondensed
6. 6
   OtroThe crude mixture was purified by silica gel chromatography (1% MeOH/CH2Cl2+0.1% Et3N)

Procedimiento

A solution of tert-butyl 8-bromo-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (449.7 mg, 1.28 mmol) and powdered potassium hydroxide (86.9 mg, 1.54 mmol) in acetone (4.0 ml) was stirred for 15 minutes before the addition of 2-(phenoxymethyl)oxirane (254 mg, 1.69 mmol). After 1 h the reaction was condensed, diluted with EtOAc and washed twice with water and then brine. The organic layer was then dried over Na2SO4, filtered and condensed. The crude mixture was purified by silica gel chromatography (1% MeOH/CH2Cl2+0.1% Et3N). Yield=21%. ESI (m/z): 546.6 (M+CHCOO−).

Fuente