反応 #76302

反応方程式

[4-(4-chloro-1-oxobutyl)phenyl]methyl-propanedioic acid, dimethyl ester

potassium carbonate

α-(4-pyridyl)benzhydrol

→

title compound

収率 76.0%

[4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]1-oxobutyl]phenyl]methyl-propanedioic acid, dimethyl ester

収率 76.0%

溶媒

water

toluene

water

ethyl acetate

反応条件

後処理

1. 1
   温度Heat the mixture
2. 2
   温度to reflux
3. 3
   洗浄Wash the organic phase with brine
4. 4
   乾燥dry over anhydrous magnesium sulfate
5. 5
   濃縮concentrate
6. 6
   その他Purify by flash chromatography (150 g of silica gel, 10% methanol/chloroform as eluent)

実験手順

Mix together [4-(4-chloro-1-oxobutyl)phenyl]methyl-propanedioic acid, dimethyl ester (300 mg, 0.92 mmol), potassium carbonate (350 mg, 2.5 mmol), α-(4-pyridyl)benzhydrol (500 mg, 1.9 mmol), water (3 mL) and toluene (7 mL). Heat the mixture to reflux. After 5 days, cool to room temperature. Add ethyl acetate and water. Wash the organic phase with brine, dry over anhydrous magnesium sulfate and concentrate. Purify by flash chromatography (150 g of silica gel, 10% methanol/chloroform as eluent) to give the title compound (387 mg, 76%). Additionally, compounds derived from all permutations of substituents as set forth in the illustrative examples following Step F can be prepared by the synthetic procedure depicted in Step H.

出典