Реакция #1106677

Уравнение реакции

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

Растворители

THF

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was heated
2. 2
   Температураto reflux overnight
3. 3
   ТемператураThe reaction was cooled to room temperature
4. 4
   ЭкстракцияThe solution was extracted with ethyl acetate (3×100 mL)
5. 5
   СушкаThe combined organic solution was dried over MgSO4
6. 6
   КонцентрированиеThe solution was concentrated under vacuum
7. 7
   Другоеpurified by chromatography (2% to 8% methanol in dichloromethane)

Методика

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.

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