反応 #78072

反応方程式

4-fluorobenzyl bromide

ethyl acetate

O-tert-butyl (1-acetylpiperidin-4-yl)carbamate

sodium hydride

→

O-tert-butyl N-(4-fluorobenzyl)-N-(1-acetylpiperidin-4-yl)carbamate

溶媒

water

N,N-dimethylformamide

反応条件

後処理

1. 1
   workup.STIRRINGAfter additional stirring for 4 hours
2. 2
   その他An organic phase was separated
3. 3
   洗浄washed with water and brine
4. 4
   乾燥After drying with magnesium sulfate
5. 5
   その他the solvents were removed under reduced pressure
6. 6
   その他A residue was purified by column chromatography (silica gel 100 ml, toluene:ethyl acetate=1:1 to 1:2)
7. 7
   その他After crystallization from diisopropyl ether and n-hexane

実験手順

To a solution of O-tert-butyl (1-acetylpiperidin-4-yl)carbamate (0.97 g) in N,N-dimethylformamide (10 ml) was added 60% sodium hydride (0.18 g) at ambient temperature. After stirring for 40 minutes, 4-fluorobenzyl bromide (0.6 ml) was added to the reaction mixture. After additional stirring for 4 hours, the reaction mixture was poured into a mixture of ethyl acetate (50 ml) and water (10 ml). An organic phase was separated and washed with water and brine. After drying with magnesium sulfate, the solvents were removed under reduced pressure. A residue was purified by column chromatography (silica gel 100 ml, toluene:ethyl acetate=1:1 to 1:2). After crystallization from diisopropyl ether and n-hexane, O-tert-butyl N-(4-fluorobenzyl)-N-(1-acetylpiperidin-4-yl)carbamate (922 mg) was obtained.

出典