反応 #78924

反応方程式

3-piperidinemethanol

1-(4-chlorophenyl)-1-cyclobutanecarboxylic acid

diisopropylethylamine

PyBroP

→

amide

収率 43.4%

1-[1-(4-chloro-phenyl)-cyclobutanecarbonyl]-piperidin-3-ylmethyl alcohol

収率 43.4%

溶媒

dichloromethane

反応条件

後処理

1. 1
   workup.WAITat room temperature for 4 h
2. 2
   洗浄The reaction mixture was washed successively with water, 1 N HCl, water, sat. sodium bicarbonate solution, and water (100 mL each)
3. 3
   乾燥The organic layer was dried over anhydrous sodium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated by rotary evaporation
6. 6
   その他The residue was purified by chromatography on silica gel
7. 7
   洗浄eluting with dichloromethane/methanol (96:4)

実験手順

To a solution of 3-piperidinemethanol (5.0 g, 43.4 mmol), 1-(4-chlorophenyl)-1-cyclobutanecarboxylic acid (9.14 g, 43.4 mmol), and diisopropylethylamine (11.22 g, 86.8 mmol) in dichloromethane (100 mL) at 0° C. was added PyBroP® (22.26 g, 47.8 mmol). The reaction was stirred at 0° C. for 1 h and then at room temperature for 4 h. The reaction mixture was washed successively with water, 1 N HCl, water, sat. sodium bicarbonate solution, and water (100 mL each). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation. The residue was purified by chromatography on silica gel, eluting with dichloromethane/methanol (96:4) to give 5.8 g of the amide 1 as a thick gum.

出典