反応 #157970

反応方程式

Tert-butyl 4-[(benzyloxy)methyl]-3,6-dihydropyridine-1(2H)-carboxylate

diethyl zinc

di-tert-butyl dicarbonate

ammonium chloride

TFA

diiodomethane

→

tert-butyl 6-[(benzyloxy)methyl]-3-azabicyclo[4.I.0]heptane-3-carboxylate

溶媒

dichloromethane

dichloromethane

triethylamine

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   workup.STIRRINGfurther stirring
2. 2
   workup.WAITwas performed at the same temperature for 40 minutes
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITwas performed at room temperature for 15 hours
5. 5
   workup.ADDITIONwas added
6. 6
   workup.STIRRINGstirring
7. 7
   workup.WAITwas performed at room temperature for 5 hours
8. 8
   抽出extraction
9. 9
   洗浄by washing with saturated brine
10. 10
    乾燥drying over anhydrous magnesium sulfate
11. 11
    その他The residue obtained by concentration under reduced pressure
12. 12
    その他was purified by silica gel column chromatography (EtOAc/hexane)

実験手順

Under an argon atmosphere, after diethyl zinc (1.0M hexane solution: 27.0 ml) was added to dichloromethane (40 ml) with ice cooling, a TFA (2 ml)/dichloromethane (10 ml) solution was added dropwise, and stirring was performed under ice cooling for 40 minutes. Then, after a diiodomethane (7.24 g)/dichloromethane (10 ml) solution was added dropwise and further stirring was performed at the same temperature for 40 minutes. Tert-butyl 4-[(benzyloxy)methyl]-3,6-dihydropyridine-1(2H)-carboxylate (3.28 g)/dichloromethane (30 ml) solution was added dropwise, and stirring was performed at room temperature for 15 hours. After adding triethylamine under ice cooling and adjusting pH to 7 to 8, di-tert-butyl dicarbonate (2.83 g) was added, and stirring was performed at room temperature for 5 hours. A saturated ammonium chloride aqueous solution was added, extraction was performed with chloroform, followed by washing with saturated brine and drying over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (EtOAc/hexane) to obtain tert-butyl 6-[(benzyloxy)methyl]-3-azabicyclo[4.I.0]heptane-3-carboxylate (2.22 g).

出典