반응 #715769

반응 방정식

Ethanolamine

2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide

pyridine

methanesulfonic anhydride

→

tert-butyl-3-(6-amino-3-methylpyridin-2-yl)benzoate

수율 53.0%

용매

acetonitrile

water

MeCN

반응 조건

후처리

1. 1
   온도while maintaining the temperature at less than 75° C
2. 2
   workup.ADDITIONafter complete addition
3. 3
   workup.STIRRINGAfter stirring for 2 hours
4. 4
   온도the mixture was cooled to 10° C
5. 5
   workup.STIRRINGAfter stirring for 3 hours
6. 6
   여과the solid was collected by filtration
7. 7
   세척washed with water (3 vol), 2:1 acetonitrile/water (3 vol), and acetonitrile (2×1.5 vol)
8. 8
   건조The solid was dried to constant weight (less than 1% difference) in a vacuum oven at 50° C. with a slight N2

실험 절차

A solution of 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (1 eq) and pyridine (4 eq) in acetonitrile (8 vol) was heated to 70° C. A solution of methanesulfonic anhydride (1.5 eq) in MeCN (2 vol) was added over 50 minutes via addition funnel while maintaining the temperature at less than 75° C. The mixture was stirred for an additional 0.5 hours after complete addition. The mixture was then allowed to cool to ambient temperature. Ethanolamine (10 eq) was added via addition funnel. After stirring for 2 hours, water (6 vol) was added, and the mixture was cooled to 10° C. After stirring for 3 hours, the solid was collected by filtration and washed with water (3 vol), 2:1 acetonitrile/water (3 vol), and acetonitrile (2×1.5 vol). The solid was dried to constant weight (less than 1% difference) in a vacuum oven at 50° C. with a slight N2 bleed to afford tert-butyl-3-(6-amino-3-methylpyridin-2-yl)benzoate as a red-yellow solid (53% yield).

출처