Реакция #1690

Уравнение реакции

2-methoxycarbonyl-(1RS,4aSR,8aSR)-perhydoisoquinoline-1-carboxylic acid t-butyl ester

sodium ethoxide

→

title compound

Выход 95.2%

2-Methoxycarbonyl-(1RS,4aRS,8aRS)-perhydoisoquinoline-1-carboxylic acid ethyl ester

Выход 95.2%

Растворители

EtOH

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture was refluxed (24 h)
2. 2
   ДругоеThe organic solvent was evaporated in vacuo, ethyl acetate (400 mL) and water (100 mL)
3. 3
   workup.ADDITIONwas added to the residue
4. 4
   ДругоеThe organic layer was separated
5. 5
   Промывкаwashed twice with water
6. 6
   Сушкаdried (MgSO4)
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеthe filtrate was concentrated in vacuo

Методика

To a solution of 2-methoxycarbonyl-(1RS,4aSR,8aSR)-perhydoisoquinoline-1-carboxylic acid t-butyl ester (81.2 g, 273 mmol) in EtOH (500 mL) was added sodium ethoxide (21% in ethanol) (88.4 mL, 273 mmol) and the reaction mixture was refluxed (24 h). The organic solvent was evaporated in vacuo, ethyl acetate (400 mL) and water (100 mL) was added to the residue. The organic layer was separated, washed twice with water, dried (MgSO4), filtered, and the filtrate was concentrated in vacuo to afford an oil of pure title compound (70 g,0.95%); FAB-MS 270 (MH+); TLC Rf (A) 0.61.

Источник