تفاعل #1690

معادلة التفاعل

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

sodium ethoxide

→

title compound

المردود 95.2%

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

المردود 95.2%

المذيبات

EtOH

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was refluxed (24 h)
2. 2
   أخرىThe organic solvent was evaporated in vacuo, ethyl acetate (400 mL) and water (100 mL)
3. 3
   workup.ADDITIONwas added to the residue
4. 4
   أخرىThe organic layer was separated
5. 5
   غسيلwashed twice with water
6. 6
   تجفيفdried (MgSO4)
7. 7
   ترشيحfiltered
8. 8
   تركيزthe filtrate was concentrated in vacuo

الإجراء التجريبي

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.

المصدر