Реакция #54756

Уравнение реакции

3,3-Dimethylallyl bromide

4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline

sodium hydride

water

→

N-(3,3-dimethylallyl)-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

Выход 94.4%

Растворители

dimethylformamide

dimethylformamide

dimethylformamide

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture was heated for 1 hour
2. 2
   workup.ADDITIONafter the addition
3. 3
   Температураcooled to 25°
4. 4
   ТемператураAfter heating at 80° for 1 hour it
5. 5
   Экстракцияextracted with ether

Методика

A solution of 4 g (14.7 mmoles) of 4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline in 50 ml of anhydrous dimethylformamide was added dropwise to 700 mg of a 55% suspension of sodium hydride in mineral oil in 50 ml of dimethylformamide at 70°. The reaction mixture was heated for 1 hour after the addition was complete and then cooled to 25°. 3,3-Dimethylallyl bromide (2.37 g, 15.8 mmoles) in 10 ml of dimethylformamide was added dropwise and the solution stirred overnight at 25°. After heating at 80° for 1 hour it was poured into water and extracted with ether to yield 4.74 g of N-(3,3-dimethylallyl)-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline (oil), which was evaporatively distilled, bp 225° (0.005 mm).

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