反应详情

To a solution of oxalyl dichloride (78 μL, 0.87 mmol) in DCM (1.5 mL) at −60° C. was added a solution of DMSO (93 μL, 1.30 mmol) in DCM (1.5 mL) under N2. After being stirred for 2 min, a solution of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((3S)-2-hydroxypentan-3-yl)-3-methylpiperidin-2-one prepared in example 151, Step C (200 mg, 0.434 mmol) in DCM (1.5 mL) was added and the resulting solution was stirred for 15 min. at −60° C. Then, triethylamine (305 μL, 2.17 mmol) was added to the reaction solution. After being stirred at rt for 20 min, the reaction was quenched (water), extracted (2×EtOAc), and washed (2×sat. aq. NaCl solution). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Purification by combi flash (SiO2, 24 g, 20% and 30% EtOAc/Hexanes) provided the title compound as a colorless foam.

1. stirringthe resulting solution was stirred for 15 min. at −60° C
2. stirringAfter being stirred at rt for 20 min
3. customthe reaction was quenched (water)
4. extractionextracted (2×EtOAc)
5. washwashed (2×sat. aq. NaCl solution)
6. dry with materialThe combined organic layers were dried (Na2SO4)
7. concentrationconcentrated under reduced pressure
8. customPurification by combi flash (SiO2, 24 g, 20% and 30% EtOAc/Hexanes)