反应 #1702170

反应方程式

triethylamine

4-chlorobenzaldehyde

sodium triacetoxyborohydride

→

N-benzylpiperidine

溶剂

methylene chloride

ethyl acetate

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

Racemic 3-bromo-4,5-dihydroisoxazole III-43 was dissolved in trifluoroacetic acid (0.20 M with respect to isoxazole) and stirred at room temperature for 1 h. The solvent is then removed under vacuum and the crude residue is azeotroped with toluene (2×) to provide a the trifluoroacetic acid salt as a white solid which is then is dissolved in methylene chloride (0.06 M with respect to isoxozaole) after which triethylamine (2.5 equiv) and 4-chlorobenzaldehyde (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-45 as a white solid. These compounds can be separated using chiral HPLC methods known in the art. For example, see chiral HPLC Method disclosed herein. [M+H]+=316.6 m/z. Activity: C

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