反应 #1702169

反应方程式

sodium triacetoxyborohydride

3-Bromo-4,5-dihydroisoxazole

triethylamine

benzaldehyde

→

N-benzylpiperidine

溶剂

ethyl acetate

methylene chloride

反应条件

后处理

1. 1
   workup.ADDITIONare added
2. 2
   洗涤washed with dilute NaOH
3. 3
   干燥The organic layer is then dried over sodium sulfate
4. 4
   浓缩concentrated under vacuum
5. 5
   其他to provide crude material which
6. 6
   其他was purified

实验过程

3-Bromo-4,5-dihydroisoxazole III-14 is dissolved in methylene chloride (0.06 M with respect to isxozaole) after which triethylamine (2.5 equiv) and benzaldehyde (1.25 equiv) are added followed by sodium triacetoxyborohydride (1.5 equiv). The reaction is allowed to stir for 16 h after which point is diluted with ethyl acetate and washed with dilute NaOH and then brine. The organic layer is then dried over sodium sulfate and concentrated under vacuum to provide crude material which was purified using flash silica gel chromatography (ethyl acetate/hexanes) to provide N-benzylpiperidine III-19 as a white solid. [M−H]−=308.1 m/z. Activity: A.

来源