反応 #1367014

反応方程式

4-(4-pyridinyl)piperidine

ethyl 5-{(1R)-1 -[2-(tert-butoxy)-2-oxoethyl]4-cyclohexylbutyl}-1,2,4-oxadiazole-3-carboxylate

4-(4-pyridinyl)piperidine

→

title compound

収率 60.1%

tert-Butyl (3R)-6-cyclohexyl-3-(3-{[4-(4-pyridinyl)-1-piperidinyl]carbonyl}-1,2,4-oxadiazol-5-yl)hexanoate

収率 60.1%

溶媒

ethanol

反応条件

後処理

1. 1
   温度the resulting mixture was heated
2. 2
   温度under reflux under a nitrogen atmosphere for 72 hours
3. 3
   温度the mixture heated
4. 4
   温度under reflux for 24 hours
5. 5
   その他The solvent was removed under reduced pressure
6. 6
   その他the residue was partitioned between ethyl acetate and water
7. 7
   その他The layers were separated
8. 8
   抽出the aqueous layer extracted with ethyl acetate
9. 9
   洗浄The combined organic layers were washed sequentially with water and brine
10. 10
    乾燥dried over anhydrous sodium sulphate
11. 11
    ろ過filtered
12. 12
    その他the solvent removed under reduced pressure
13. 13
    その他The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (99:1)

実験手順

A solution of ethyl 5-{(1R)-1 -[2-(tert-butoxy)-2-oxoethyl]4-cyclohexylbutyl}-1,2,4-oxadiazole-3-carboxylate (Preparation 3) (0.50 g, 1.27 mmol) in ethanol (10 ml) was treated with 4-(4-pyridinyl)piperidine (Monatsh.Chem.; 3; 1882; 867) (0.41 g, 2.54 mmol) and the resulting mixture was heated under reflux under a nitrogen atmosphere for 72 hours. Further 4-(4-pyridinyl)piperidine (0.21 g, 1.27 mmol) was added and the mixture heated under reflux for 24 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed sequentially with water and brine, dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (99:1) gradually changing to dichloromethane:methanol (95:5) to afford the title compound as a pale yellow oil (0.39 g).

出典