Реакция #54753

Уравнение реакции

cyclopropylmethyl bromide

water

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

sodium hydride

→

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

Растворители

dimethylformamide

benzene

dimethylformamide

dimethylformamide

Условия реакции

Обработка

1. 1
   Температураheated at 70°
2. 2
   ТемператураHeating
3. 3
   workup.ADDITIONafter the addition
4. 4
   workup.ADDITIONwas added
5. 5
   ТемператураThe reaction mixture was heated at 80° for 2 hours
6. 6
   workup.WAITto stand at 25° overnight
7. 7
   Экстракцияextracted with ether
8. 8
   ДругоеEvaporation of the ether
9. 9
   Другоеgave an oil which

Методика

A solution of 2.0 g (7.3 mmoles) of 4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline (Ex. 7A) in 50 ml of anhydrous dimethylformamide was added to 35.1 mg of a 55% suspension of sodium hydride in mineral oil in 25 ml of dimethylformamide heated at 70°. Heating was continued for 45 minutes after the addition was complete after which time 1.09 g (8.1 mmoles) of cyclopropylmethyl bromide in 10 ml of dimethylformamide was added. The reaction mixture was heated at 80° for 2 hours and allowed to stand at 25° overnight. It was poured into water and extracted with ether. Evaporation of the ether gave an oil which showed one spot by thin-layer chromatography (silica gel plates, benzene solvent, Rf 0.4, starting material had Rf 0.07) and was identified by nmr as N-cyclopropylmethyl-4a(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline.

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