반응 #40869

반응 방정식

NaHCO3

[(R)-1-formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester

(diethoxy-phosphoryl)-acetic acid ethyl ester

n-butyllithium

→

title compound

(E)-(R)-4-tert-butoxycarbonylamino-6-(4-heptyloxy-phenyl)-4-methyl-hex-2-enoic acid ethyl ester

용매

AcOEt

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITis continued at −78° C. for 1.5 hours
3. 3
   온도to warm to RT
4. 4
   workup.STIRRINGstirred at RT for 2 hours
5. 5
   추출the aqueous phase is extracted twice with AcOEt
6. 6
   건조The combined organic layers are dried (Na2SO4)
7. 7
   농축concentrated under reduced pressure
8. 8
   세척Column chromatography eluting with 4% AcOEt in toluene

실험 절차

To a stirred solution of (diethoxy-phosphoryl)-acetic acid ethyl ester (429 mg, 1.92 mMol) in dry THF (7 ml) is added n-butyllithium (0.66 ml, 2.5M in hexane, 1.66 mMol) at −78° C. The mixture was stirred at −78° C. for 1 hour. After that time, a solution of [(R)-1-formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester (500 mg, 1.28 mMol) in THF (4 ml) is added and stirring is continued at −78° C. for 1.5 hours. The mixture is allowed to warm to RT and then stirred at RT for 2 hours. The reaction mixture is then poured onto a biphasic mixture of AcOEt and NaHCO3 (saturated aqueous solution) and the aqueous phase is extracted twice with AcOEt. The combined organic layers are dried (Na2SO4) and concentrated under reduced pressure. Column chromatography eluting with 4% AcOEt in toluene gives the title compound as a colourless oil.

출처