반응 #360374

반응 방정식

diethyl azodicarboxylate

(+/−)-(3RS,4SR)-N-benzyloxy-N-[4-butyl-1-(4-hydroxybenzyl)-2-oxopyrrolidin-3-yl-methyl]formamide

furan-2-yl-methanol

triphenylphosphine

→

(+/−)-(3RS,4SR)-N-benzyloxy-N-{4-butyl-1-[4-(furan-2-yl- methoxy)benzyl]-2-oxopyrrolidin-3-yl-methyl}formamide

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도The reaction mixture was warmed up to rt
2. 2
   기타The reaction was quenched with saturated aqueous NaHCO3 (10 mL)
3. 3
   추출extracted with dichloromethane (3×10 mL)
4. 4
   추출The combined extractions
5. 5
   건조were dried (Na2SO4)
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타The residue was purified by flash column chromatography (silica gel, ethyl acetate/hexanes 1:1)

실험 절차

To a solution of (+/−)-(3RS,4SR)-N-benzyloxy-N-[4-butyl-1-(4-hydroxybenzyl)-2-oxopyrrolidin-3-yl-methyl]formamide (0.1 g, 0.24 mmol) in tetrahydrofuran (3 mL) under argon was added furan-2-yl-methanol (0.041 mL, 0.048 mmol) and triphenylphosphine (0.07 g, 0.27 mmol). The solution was cooled to 0° C. and diethyl azodicarboxylate (0.042 mL, 0.27 mmol) was added dropwise. The reaction mixture was warmed up to rt and stirred overnight. The reaction was quenched with saturated aqueous NaHCO3 (10 mL) and extracted with dichloromethane (3×10 mL). The combined extractions were dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography (silica gel, ethyl acetate/hexanes 1:1) to afford (+/−)-(3RS,4SR)-N-benzyloxy-N-{4-butyl-1-[4-(furan-2-yl- methoxy)benzyl]-2-oxopyrrolidin-3-yl-methyl}formamide as a colorless oil (0.075 g, 63%). MS(ES) m/e 491 [M+H]+.

출처