반응 #44656

반응 방정식

diisopropyl azodicarboxylate

(R)-1-[(3R,5R)-5-(4-chlorophenyl)morpholine-3-yl]ethanol

triphenylphosphine

4-nitrobenzoic acid

→

titled compound

수율 100.0%

4-nitrobenzoic acid (S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholine-3-yl]ethyl ester

수율 100.0%

용매

water

ethyl acetate

tetrahydrofuran

반응 조건

후처리

1. 1
   온도while cooling with ice
2. 2
   기타the organic layer was partitioned
3. 3
   세척The organic layer was washed with brine
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   기타Solvent was removed by distillation under reduced pressure
6. 6
   기타the resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→8/2→7/3)

실험 절차

Under a nitrogen atmosphere, to a tetrahydrofuran (20 mL) solution containing (R)-1-[(3R,5R)-5-(4-chlorophenyl)morpholine-3-yl]ethanol (903 mg), triphenylphosphine (1.81 g) and 4-nitrobenzoic acid (1.16 g) was dropwise added diisopropyl azodicarboxylate (1.36 mL) while cooling with ice. The resultant solution was stirred at the same temperature for 30 minutes, and then at room temperature for 2 hours. The reaction solution was diluted with water and ethyl acetate, and the organic layer was partitioned. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→8/2→7/3), to thereby obtain the titled compound (1.46 g). The physical properties of the compound were as follows.

출처