반응 #1987377

반응 방정식

2-(4-cyanophenoxy)-1-methylethylamine

N-methylpiperidine

2-tert-butoxycarbonylamino-3-methyl-3-butenic acid

isobutyl chloroformate

→

desired product

수율 32.0%

2-tert-butoxycarbonylamino-3-methyl-N-[2-(4-cyanophenoxy)-1-methylethyl]-3-butenic acid amide

수율 32.0%

용매

Water

methylene chloride

반응 조건

후처리

1. 1
   workup.ADDITIONwas added to the mixture at -40° C.
2. 2
   온도warm naturally to room temperature
3. 3
   workup.STIRRINGwhile being stirred
4. 4
   workup.STIRRINGwas stirred for 20 hours at room temperature
5. 5
   세척After the methylene chloride layer was washed successively with a 5% aqueous solution of sodium bicarbonate and water
6. 6
   건조the organic layer was dried over anhydrous magnesium sulfate
7. 7
   기타the methylene chloride was removed under reduced pressure
8. 8
   기타The obtained crude crystal
9. 9
   기타was purified by column chromatography on silica gel

실험 절차

0.5 g of N-methylpiperidine was added to a solution containing 1.1 g of 2-tert-butoxycarbonylamino-3-methyl-3-butenic acid dissolved in 40 ml of methylene chloride, at -20° C. After the mixture was stirred for 10 minutes at the same temperature, 0.7 g of isobutyl chloroformate was added to the mixture at -40° C., and stirred for 1 hour at -20° C. 1.9 g of 2-(4-cyanophenoxy)-1-methylethylamine was added to this mixture at -60° C., and then the reaction mixture was allowed to sit and warm naturally to room temperature while being stirred, and was stirred for 20 hours at room temperature. Water was subsequently added to the reaction mixture. After the methylene chloride layer was washed successively with a 5% aqueous solution of sodium bicarbonate and water, the organic layer was dried over anhydrous magnesium sulfate and the methylene chloride was removed under reduced pressure. The obtained crude crystal was purified by column chromatography on silica gel, thus obtaining 0.3 g of the desired product in the form of a colorless glutinous substance (yield: 32%).

출처