反応 #1559939

反応方程式

piperidin-4-ylmethyl 2-hydroxy-2,2-diphenylacetate

4-((5-(1,3-dioxolan-2-yl)pentyl)oxy)benzaldehyde

sodium triacetoxyborohydride

→

title compound

収率 70.9%

(1-(4-((5-(1,3-dioxolan-2-yl)pentyl)oxy)benzyl)piperidin-4-yl)methyl 2-hydroxy-2,2-diphenylacetate

収率 70.9%

溶媒

DCM

反応条件

後処理

1. 1
   その他The reaction mixture was partitioned between EtOAc and saturated sodium hydrogen carbonate
2. 2
   乾燥The organic phase was dried (sodium sulfate)
3. 3
   ろ過filtered
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他The crude material was purified by silica gel column chromatography
6. 6
   洗浄eluting with 1 to 10% methanol in ethyl acetate

実験手順

To a stirred solution of piperidin-4-ylmethyl 2-hydroxy-2,2-diphenylacetate (0.4 g, 1.23 mmol) and 4-((5-(1,3-dioxolan-2-yl)pentyl)oxy)benzaldehyde (0.38 g, 1.44 mmol) in DCM (5 mL) was added sodium triacetoxyborohydride (0.388 g, 1.83 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between EtOAc and saturated sodium hydrogen carbonate. The organic phase was dried (sodium sulfate), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with 1 to 10% methanol in ethyl acetate to afford the title compound as a colourless oil (0.50 g, 26%).

出典