반응 #82363

반응 방정식

tert.butylamine

N-ethylmorpholine

isobutyl chloroformate

2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxylic acid

→

tert.butyl 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido-[3,4-b]indole-1-carboxamide

용매

ethyl acetate

tetrahydrofuran

반응 조건

후처리

1. 1
   기타while protecting with a drying tube, in an ice/acetone bath
2. 2
   workup.STIRRINGThe mixture was then stirred at 0° C. for 40 minutes and at room temperature for 45 minutes
3. 3
   세척washed twice with water, twice with 0.5M sodium hydroxide solution and again with water
4. 4
   건조The solution was dried over magnesium sulphate
5. 5
   기타evaporated to dryness
6. 6
   기타Recrystallization from ethyl acetate and n-hexane

실험 절차

A solution of 4.54 g of 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxylic acid in 45 ml of anhydrous tetrahydrofuran was cooled, while protecting with a drying tube, in an ice/acetone bath. 1.82 ml of N-ethylmorpholine and 1.82 ml of isobutyl chloroformate were added, the mixture was stirred for 10 minutes and then 2.1 ml of tert.butylamine were added. The mixture was then stirred at 0° C. for 40 minutes and at room temperature for 45 minutes, diluted with ethyl acetate and washed twice with water, twice with 0.5M sodium hydroxide solution and again with water. The solution was dried over magnesium sulphate and evaporated to dryness. Recrystallization from ethyl acetate and n-hexane gave 1.21 g of tert.butyl 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido-[3,4-b]indole-1-carboxamide; MS: m/e 406 [M+H]+. A further 0.76 g of identical material was obtained by subjecting the mother liquors to chromatography on silica gel using ethyl acetate/n-hexane (1:1) for the elution.

출처