Реакция #652839

Уравнение реакции

HCl

sodium hydrogen carbonate

tert-butyl [2-[[4-(formylmethyl)-1-piperidinyl]methyl]-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-5-yl]carbamate

1,1-diphenylmethylamine

sodium cyanoborohydride

bromocresol green

→

title compound

Выход 77.0%

Tert-butyl [2-[[4-[2-[(diphenylmethyl)amino]ethyl]-1-piperidinyl]methyl]-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-5-yl]carbamate

Выход 77.0%

Растворители

ethanol

ethanol

Условия реакции

Обработка

1. 1
   ЭкстракцияThe mixture was extracted with ethyl acetate
2. 2
   Промывкаthe extract was washed with saturated aqueous NaCl
3. 3
   Сушкаdried over MgSO4
4. 4
   workup.DISTILLATIONThe solvent was then distilled off under reduced pressure
5. 5
   Другоеthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=4:1 to ethyl acetate)

Методика

A solution of tert-butyl [2-[[4-(formylmethyl)-1-piperidinyl]methyl]-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-5-yl]carbamate (1.5 g) and 1,1-diphenylmethylamine (0.60 mL) in ethanol (20 mL) was stirred on an ice bath for 30 minutes. Then, 0.26 g of sodium cyanoborohydride and a small amount of bromocresol green were added. Thereafter, 4N-HCl solution in ethanol was added until the reaction mixture had turned yellow. The mixture was stirred for 1 hour, after which it was poured in an excess of aqueous sodium hydrogen carbonate. The mixture was extracted with ethyl acetate and the extract was washed with saturated aqueous NaCl and dried over MgSO4. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=4:1 to ethyl acetate) to provide 1.6 g of the title compound. Yield 77%.

Источник