Реакция #541908

Уравнение реакции

tetrabutylammonium fluoride tetrahydrofuran

tetrahydrofuran

methyl 2-(2-(benzyloxy)-5-(1-(2-(tert-butyldimethylsilyloxy)ethyl)piperidin-4-yl)benzamido)-4-phenylbenzoate

water

→

methyl 2-(2-(benzyloxy)-5-(1-(2-hydroxyethyl)piperidin-4-yl)benzamido)-4-phenylbenzoate

Выход 78.6%

Растворители

ethyl acetate

Условия реакции

Обработка

1. 1
   ТемператураUnder ice-cooling
2. 2
   ДругоеThe organic layer was separated
3. 3
   Промывкаwashed with a saturated aqueous solution of sodium chloride
4. 4
   Сушкаdried over anhydrous magnesium sulfate
5. 5
   Другоеthe solvent was evaporated under reduced pressure
6. 6
   ДругоеThe obtained residue was purified by silica gel column chromatography [eluent: 100-92% chloroform/methanol]

Методика

A 1.0 mol/L tetrabutylammonium fluoride-tetrahydrofuran solution (0.38 mL) was added to a tetrahydrofuran (1.3 mL) solution of the obtained methyl 2-(2-(benzyloxy)-5-(1-(2-(tert-butyldimethylsilyloxy)ethyl)piperidin-4-yl)benzamido)-4-phenylbenzoate (0.13 g), followed by stirring at room temperature for 4 hours. Under ice-cooling, water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-92% chloroform/methanol] to obtain 0.085 g of methyl 2-(2-(benzyloxy)-5-(1-(2-hydroxyethyl)piperidin-4-yl)benzamido)-4-phenylbenzoate as a white solid.

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