반응 #87155

반응 방정식

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

water

→

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

수율 49.0%

용매

EtOAc

반응 조건

후처리

1. 1
   기타The two layers were separated
2. 2
   추출the aqueous phase was extracted with EtOAc (50 mL×3)
3. 3
   세척The combined organic phases were washed with brine (50 mL×3)
4. 4
   건조dried over anhydrous sodium sulfate
5. 5
   농축concentrated
6. 6
   기타The residue was purified by flash column chromatography on silica gel (CH2Cl2/MeOH=20:1)

실험 절차

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.

출처