反应 #632036

反应方程式

hydroxylamine

water

( 29 )

(3R,4R)-2,5-Dioxo-3,4-dibenzoyloxy-3,4-dihydrofuran

acetonitrile

→

title compound ( 30 )

收率 87.1%

1-Hydroxy-(3R,4R)-2,5-Dioxo-3,4-dibenzoyloxypyrrolidine

收率 87.1%

溶剂

toluene

反应条件

后处理

1. 1
   其他To a 3-neck 5 L round bottom flask fitted with a mechanical stirrer
2. 2
   workup.DISSOLUTIONThe starting material gradually dissolved during the addition
3. 3
   温度the reaction mixture was warmed to 20° C.
4. 4
   浓缩The reaction mixture was concentrated in vacuo
5. 5
   workup.ADDITIONdiluted with EtOAc (1 L)
6. 6
   洗涤washed with 1 N HCl (2×1 L)
7. 7
   其他The organic phase was separated
8. 8
   浓缩concentrated in vacuo
9. 9
   其他to afford a viscous red syrup
10. 10
    workup.DISSOLUTIONThe syrup gradually dissolved
11. 11
    其他the product crystallized
12. 12
    温度After cooling to room temperature the solid
13. 13
    过滤was collected by filtration
14. 14
    洗涤washed with 10% acetone in hexane (2×1 L)
15. 15
    其他dried in a vacuum oven

实验过程

To a 3-neck 5 L round bottom flask fitted with a mechanical stirrer and a Teflon coated temperature probe was added (29) (2.79 mol) followed by acetonitrile (2 L). The suspension was cooled in an ice bath to 4° C., followed by the addition of 50% aqueous hydroxylamine (180 mL, 2.93 mol) over 1 h. The starting material gradually dissolved during the addition and the reaction mixture was warmed to 20° C. and stirred for 1 h. The reaction mixture was concentrated in vacuo, diluted with EtOAc (1 L) and washed with 1 N HCl (2×1 L). The organic phase was separated and concentrated in vacuo to afford a viscous red syrup. The syrup was then heated for two hours in toluene (2.5 L) at 100° C. with azeotropic removal of water. The syrup gradually dissolved and then the product crystallized. After cooling to room temperature the solid was collected by filtration, washed with 10% acetone in hexane (2×1 L) and dried in a vacuum oven to afford the title compound (30) (862 g, 2.43 mol, 87% yield) as a white solid. 1H NMR (CDCl3, 400 MHz): δ 5.85 (s, 2H), 7.45 (app. t, 4H), 7.65 (app t, 2H), 8.05 (m, 4H).

来源