反应 #1178482

反应方程式

1,4-di-O-tosyl-D-threitol

benzylamine

sodium hydrogen carbonate

→

title compound

收率 46.0%

(3R,4R)-1-benzylpyrrolidine-3,4-diol

收率 46.0%

溶剂

1,4-dioxane

反应条件

后处理

1. 1
   温度the mixture was heated
2. 2
   温度to reflux under a nitrogen stream for 4 days
3. 3
   其他was returned to room temperature
4. 4
   萃取The mixture was extracted with ethyl acetate
5. 5
   洗涤The extract was washed with saturated brine
6. 6
   干燥dried over anhydrous sodium sulfate
7. 7
   浓缩concentrated under reduced pressure
8. 8
   其他The obtained residue was purified by column chromatography

实验过程

To a 1,4-dioxane (20 mL) solution of 1,4-di-O-tosyl-D-threitol (9.15 g, 21.25 mmol), benzylamine (9.29 mL, 85.0 mmol) was added, and the mixture was heated to reflux under a nitrogen stream for 4 days while stirring. The reaction liquor was returned to room temperature, and then a saturated aqueous solution of sodium hydrogen carbonate (50 mL) was added. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by column chromatography using silica gel [NH(basic)-silica gel 100 g, ethyl acetate to chloroform/methanol (10/1)], to obtain the title compound (1.88 g, 46%) as an oily matter.

来源