Reacción #540907

Ecuación de reacción

12-epi-Salvinorin B

NaI

diisopropylethylamine

chloromethylethyl ether

→

ethoxymethyl ether

Rendimiento 65.0%

2-ethoxymethyl ether 12-epi-Salvinorin B

Rendimiento 65.0%

Disolventes

EtOAc

DMA

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was then cooled to rt
2. 2
   Lavadowashed with water and brine
3. 3
   Secadodried over MgSO4
4. 4
   OtroAfter evaporation of the solvent, flash chromatography (0% to 70% EtOAc in hexanes)

Procedimiento

12-epi-Salvinorin B (15 mg, 0.038 mmol) was dissolved in DMA (500 μL) under argon. To this solution was added NaI (23 mg, 0.15 mmol), diisopropylethylamine (37 μL, 0.21 mmol), and chloromethylethyl ether (16 μL, 0.19 mmol). This solution was warmed to 80° C., and stirred for 18 hours. The mixture was then cooled to rt and diluted with EtOAc, washed with water and brine, and dried over MgSO4. After evaporation of the solvent, flash chromatography (0% to 70% EtOAc in hexanes) gave ethoxymethyl ether 37 as an off-white solid. (11.2 mg, 65% yield); Rf 0.28 (98:2, CH2Cl2/MeOH); 1H NMR (300 MHz, CDCl3) δ 7.43 (m, 1H), 7.40 (t, J=1.7 Hz, 1H), 6.41 (m, 1H), 5.29 (dd, J=6.0, 11.6, 1H), 4.76 (q, J=7.2, 2H), 4.16 (dd, J=7.4, 12.2, 1H), 3.72 (s, 3H), 3.69-3.51 (m, 2H), 2.72 (dd, J=3.3, 13.3, 1H), 2.46-2.27 (m, 4H), 2.20 (m, 1H), 2.05-1.68 (m, 4H), 1.57 (m, 1H), 1.38 (s, 3H), 1.18 (t, J=7.1, 2H), 1.06 (s, 3H).

Fuente