Reacción #1106677

Ecuación de reacción

sodium hydroxide

Borane THF

3-Methylene-3,4-dihydro-2H-benzo[b][1,4]dioxepine

Aminosulfonic acid

→

((3,4-dihydro-2H-benzo[b][1,4]dioxepin-3-yl)methyl)amine

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was heated
2. 2
   Temperaturato reflux overnight
3. 3
   TemperaturaThe reaction was cooled to room temperature
4. 4
   ExtracciónThe solution was extracted with ethyl acetate (3×100 mL)
5. 5
   SecadoThe combined organic solution was dried over MgSO4
6. 6
   ConcentraciónThe solution was concentrated under vacuum
7. 7
   Otropurified by chromatography (2% to 8% methanol in dichloromethane)

Procedimiento

3-Methylene-3,4-dihydro-2H-benzo[b][1,4]dioxepine (5.00 g, 30.8 mmol) was dissolved in dry THF (100 mL). Borane-THF (1.0 M in THF, 10.3 mL) was added at 0° C. The reaction was stirred at RT for 5 hours. Aminosulfonic acid (6.97 g, 61.6 mmol) was added. The reaction was heated to reflux overnight. The reaction was cooled to room temperature and aqueous sodium hydroxide (3.0 M, 100 mL) was added. The solution was extracted with ethyl acetate (3×100 mL). The combined organic solution was dried over MgSO4. The solution was concentrated under vacuum and purified by chromatography (2% to 8% methanol in dichloromethane) to yield ((3,4-dihydro-2H-benzo[b][1,4]dioxepin-3-yl)methyl)amine as a colorless oil.

Fuente