反应 #87155

反应方程式

Boc-(R)-piperidine-3-carboxylic acid

water

→

(S)-1-(tert-butoxycarbonyl)-6-oxopiperidine-3-carboxylic acid

收率 49.0%

溶剂

EtOAc

反应条件

后处理

1. 1
   其他The two layers were separated
2. 2
   萃取the aqueous phase was extracted with EtOAc (50 mL×3)
3. 3
   洗涤The combined organic phases were washed with brine (50 mL×3)
4. 4
   干燥dried over anhydrous sodium sulfate
5. 5
   浓缩concentrated
6. 6
   其他The residue was purified by flash column chromatography on silica gel (CH2Cl2/MeOH=20:1)

实验过程

A solution of NaIO4 (5.6 g, 26 mmol) in water (30 mL) and RuCl3 (14 mg) were added to a solution of Boc-(R)-piperidine-3-carboxylic acid (1.5 g, 6.6 mmol) in EtOAc (30 mL). The reaction mixture was stirred overnight at ambient temperature. The two layers were separated and the aqueous phase was extracted with EtOAc (50 mL×3). The combined organic phases were washed with brine (50 mL×3), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (CH2Cl2/MeOH=20:1) to afford (S)-1-(tert-butoxycarbonyl)-6-oxopiperidine-3-carboxylic acid (790 mg, 49% yield) as a pale yellow solid.

来源