Reacción #2254173

Ecuación de reacción

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

Rendimiento 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

Rendimiento 97.9%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction was stirred at 40° C. overnight
2. 2
   OtroThe solvent was evaporated in vacuo
3. 3
   workup.ADDITIONHCl was added
4. 4
   workup.DISSOLUTIONto dissolve the residue
5. 5
   LavadoThe solution was washed with Et2O
6. 6
   ExtracciónThe solution was extracted with EtOAc (2×)
7. 7
   Lavadothe combined extracts were washed with water
8. 8
   Secadobrine and then dried over MgSO4
9. 9
   FiltraciónThe solution was filtered
10. 10
    Otrothe filtrate evaporated in vacuo

Procedimiento

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).

Fuente