반응 #329317

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

MeCN

water

MeCN

반응 조건

후처리

1. 1
   온도maintaining the temperature at less than 75° C
2. 2
   workup.ADDITIONafter complete addition
3. 3
   온도to cool to ambient
4. 4
   workup.STIRRINGAfter stirring for 2 hours
5. 5
   workup.STIRRINGAfter stirring for NLT 3 hours
6. 6
   여과the solid is collected by filtration
7. 7
   세척washed with water (3 vat), 2:1 MeCN/water (3 vol), and MeCN (2×1.5 vol)
8. 8
   건조The solid is dried to constant weight (<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 MeCN (8 vol.) is heated to 70° C. A solution of methanesulfonic anhydride (1.5 eq) in MeCN (2 vol) is added over 50 min via addition funnel maintaining the temperature at less than 75° C. The mixture is stirred for an additional 0.5 hours after complete addition. The mixture is then allowed to cool to ambient. Ethanolamine (10 eq) is added via addition funnel. After stirring for 2 hours, water (6 vol.) is added and the mixture is cooled to 10° C. After stirring for NLT 3 hours, the solid is collected by filtration and washed with water (3 vat), 2:1 MeCN/water (3 vol), and MeCN (2×1.5 vol). The solid is dried to constant weight (<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