反应详情

温度

0 °C

(3S,8S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carboxylic acid methyl ester (872 mg) was dissolved in 24 mL THF and 20 mL MeOH and 591 mg LiOH was added. The flask was flushed with nitrogen and placed under a nitrogen balloon and stirred at 0° C. 12 mL water was then added in portions while stirring, then the reaction stirred at rt 15 h. 119 mg LiOH and 6 mL water were added to the reaction and stirring continued for 2 h. 4 mL water was added and stirring continued for 30 min, then 2 mL water was added. After 1.5 h the pH was adjusted to 7 with 2% w/v aqueous citric acid and the reaction extracted with EtOAc. The organic solution was washed with brine and dried over Na2SO4 and evaporated, to give 820 mg desired compound after drying. LCMS: m/z 605 (M+1).

1. customThe flask was flushed with nitrogen
2. addition12 mL water was then added in portions
3. stirringwhile stirring
4. stirringthe reaction stirred at rt 15 h
5. addition119 mg LiOH and 6 mL water were added to the reaction
6. stirringstirring
7. addition4 mL water was added
8. stirringstirring
9. waitcontinued for 30 min
10. addition2 mL water was added
11. waitAfter 1.5 h the pH was adjusted to 7 with 2% w/v aqueous citric acid
12. extractionthe reaction extracted with EtOAc
13. washThe organic solution was washed with brine
14. dry with materialdried over Na2SO4
15. customevaporated