反应 #168346

反应方程式

NH4Cl

EtOAc

3,6-dioxabicyclo[3.1.0]hexane

benzylamine

→

trans-4-(benzylamino) tetrahydrofuran-3-ol

反应条件

后处理

1. 1
   其他The mixture was irradiated in a microwave reactor at 130° C. for 2 hours
2. 2
   过滤The resulting gummy precipitate was filtered over a celite bed
3. 3
   萃取the filtrate was extracted
4. 4
   其他The organic layer was separated
5. 5
   洗涤washed with brine
6. 6
   干燥dried over anhydrous Na2SO4
7. 7
   过滤filtered
8. 8
   浓缩concentrated in vacuo
9. 9
   其他The residue was purified by reverse phase chromatography on a C-18 column (0-100% CH3CN/water)

实验过程

Ti(OiPr)4 (1.0 mL, 3.48 mmol) was added to a solution of 3,6-dioxabicyclo[3.1.0]hexane (1.5 g, 17.4 mmol) in benzylamine (2.0 mL). The mixture was irradiated in a microwave reactor at 130° C. for 2 hours. It was cooled to room temperature, and 50 mL of saturated aqueous NH4Cl solution and 20 mL of EtOAc were added to the reaction. The mixture was stirred for 10 minutes. The resulting gummy precipitate was filtered over a celite bed, and the filtrate was extracted using EtOAc (100 mL). The organic layer was separated, washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by reverse phase chromatography on a C-18 column (0-100% CH3CN/water) to afford trans-4-(benzylamino) tetrahydrofuran-3-ol. MS APCl calc'd for C11H15NO2 [M+H]+ 194. found 194.

来源