반응 #2254173

반응 방정식

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

수율 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

수율 97.9%

용매

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction was stirred at 40° C. overnight
2. 2
   기타The solvent was evaporated in vacuo
3. 3
   workup.ADDITIONHCl was added
4. 4
   workup.DISSOLUTIONto dissolve the residue
5. 5
   세척The solution was washed with Et2O
6. 6
   추출The solution was extracted with EtOAc (2×)
7. 7
   세척the combined extracts were washed with water
8. 8
   건조brine and then dried over MgSO4
9. 9
   여과The solution was filtered
10. 10
    기타the filtrate evaporated in vacuo

실험 절차

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).

출처