Réaction #2389093

Équation de réaction

tetrafluorophthalic anhydride

(S)-α-methylbenzylamine

→

desired product

Rendement 65.3%

(S)-2-(1-cyclohexylethyl)-4,5,6,7-tetrafluoro-1H-isoindole-1,3-dione

Rendement 65.3%

Solvants

chloroform

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooled
2. 2
   Autrepurified by silica gel column chromatography (eluent; methylene chloride:methanol=30:1 v/v)
3. 3
   Autrerecrystallized from a mixed solvent of n-hexane-ethyl acetate

Mode opératoire

220 mg of tetrafluorophthalic anhydride and 127 mg of (S)-α-methylbenzylamine were charged in an egg-plant type flask of 50 ml, followed by stirring under heating at a temperature of 180° C. for 1.5 hours. After cooled, the reaction product was dissolved in chloroform, purified by silica gel column chromatography (eluent; methylene chloride:methanol=30:1 v/v), recrystallized from a mixed solvent of n-hexane-ethyl acetate, to obtain 215 mg of the desired product as a colorless powder. Yield: 65%. m.p. 147-148° C.; [α]20D=5.26° (C=0.618 AcOEt); MS(EI+) 329(M)+

Source