Реакция #2254173

Уравнение реакции

BnCl

2

((2S,3S,4aR,8R,8aR)-2,3-Dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)methanol Hydrochloride

K2CO3

→

title compound

Выход 97.9%

((2S,3S,4aR,8R,8aR)-6-Benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)methanol

Выход 97.9%

Растворители

DMF

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe reaction was stirred at 40° C. overnight
2. 2
   ДругоеThe solvent was evaporated in vacuo
3. 3
   workup.ADDITIONHCl was added
4. 4
   workup.DISSOLUTIONto dissolve the residue
5. 5
   ПромывкаThe solution was washed with Et2O
6. 6
   ЭкстракцияThe solution was extracted with EtOAc (2×)
7. 7
   Промывкаthe combined extracts were washed with water
8. 8
   Сушкаbrine and then dried over MgSO4
9. 9
   ФильтрацияThe solution was filtered
10. 10
    Другоеthe filtrate evaporated in vacuo

Методика

To a solution of 2 (14.85 g, 50.0 mmol) in DMF (200 mL) was added K2CO3 (17.25 g, 125 mmol) and the mixture was stirred at 40° C. for about 4 hrs. At this point, BnCl (5.7 mL, 50.0 mmol) was added in one portion and the reaction was stirred at 40° C. overnight. The solvent was evaporated in vacuo and the residue was suspended in water (600 mL) and HCl was added to dissolve the residue. The solution was washed with Et2O and then basified with Na2CO3. The solution was extracted with EtOAc (2×) and the combined extracts were washed with water and then brine and then dried over MgSO4. The solution was filtered and the filtrate evaporated in vacuo to give the title compound (17.2 g, >95%) as a colorless to very pale yellow viscous oil which was used without further purification. 1H NMR (CDCl3) 7.3 (m, 5H), 3.6-3.8 (m, 2H), 3.5 (s, 3H), 3.4 (t, 1H), 3.26 (s, 3H), 3.268 (s, 3H), 2.9 (m, 2H), 2.2 (br s, 1H), 2.05 (m, 1H), 1.85 (t, 1H), 1.28 (s, 3H), 1.26 (s, 3H).

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