반응 #58032

반응 방정식

HCl

piperidine-1,4-dicarboxylic acid mono-tert-butyl ester

diborane

hydrogen

NaOH

HCl

hydrogen

Hydrogen

→

4-Hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester

수율 100.2%

용매

THF

반응 조건

후처리

1. 1
   온도The reaction mixture was again cooled to 0° C.
2. 2
   workup.STIRRINGThe mixture was then stirred for 10 min
3. 3
   추출The aqueous solution was extracted with ethyl acetate
4. 4
   세척the organic phase washed with brine
5. 5
   기타dried
6. 6
   농축concentrated under reduced pressure

실험 절차

To a solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (19.3 g, 84.0 mmol) in THF (100 mL) was added diborane (185 mL, 1.0 M solution in THF) over a period of 10 min at 0° C. Hydrogen gas was rapidly evolved and after gas evolution had ceased the reaction was stirred at room temperature for 1 h. The reaction mixture was again cooled to 0° C., and 1 M aqueous HCl was added dropwise to the reaction mixture with further evolution of hydrogen. Addition of HCl was continued until the evolution of hydrogen had almost ceased. The mixture was then stirred for 10 min and made basic (pH 13-14) by the addition of 1 M NaOH solution. The aqueous solution was extracted with ethyl acetate, the organic phase washed with brine, dried and concentrated under reduced pressure to yield 4-Hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (18.12 g, 100%).

출처