Реакция #467732

Уравнение реакции

naphthalene-2-boronic acid

1-phenoxycarbonyl-2-methyl-4-trifluoromethanesulfonyloxy-1,2,3,6-tetrahydropyridine

lithium chloride

→

title compound

Выход 50.0%

1-phenoxycarbonyl-2-methyl-4-(naphth-2-yl)-1,2,3,6-tetrahydropyridine

Выход 50.0%

Растворители

ethyl acetate

sodium carbonate

sodium carbonate

dimethoxyethane

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураat reflux for about 18 hours
3. 3
   ДругоеThe phases were separated
4. 4
   Промывкаthe organic phase was washed with saturated aqueous sodium chloride
5. 5
   Сушкаdried over sodium sulfate
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   Промывкаeluting with hexane containing 10% ethyl acetate
8. 8
   workup.ADDITIONFractions containing product
9. 9
   Концентрированиеconcentrated under reduced pressure

Методика

A mixture of 5.46 gm (31.8 mMol) naphthalene-2-boronic acid, 8.28 gm (22.7 mMol) 1-phenoxycarbonyl-2-methyl-4-trifluoromethanesulfonyloxy-1,2,3,6-tetrahydropyridine, 0.741 gm (0.91 mMol) palladium(II) diphenylphosphino-ferrocenyl chloride, and 2.88 gm (68 mMol) lithium chloride in 25 mL 2M aqueous sodium carbonate and 96 mL dimethoxyethane was heated at reflux for about 18 hours. The reaction mixture was cooled to room temperature and was diluted with ethyl acetate and saturated aqueous sodium carbonate. The phases were separated and the organic phase was washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with hexane containing 10% ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 3.87 gm (50%) of the title compound as a viscous oil.

Источник