1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86651614, compound

Participants

Reaction Conditions

Reaction Steps

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.185 mL, 1.24 mmol, Aldrich) was added dropwise to a suspension of Lithium chloride (55.6 mg, 1.31 mmol, Aldrich) and Methyl [bis(methyloxy)phosphoryl]{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}acetate (Tetrahedron Lett. 1981, 22, 663-666) (409 mg, 1.31 mmol) in dry Acetonitrile (20 mL) and the mixture was maintained at 0° C. for 1 h. A solution of (2R,4R)-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-4-{[(1,1-dimethylethyl)sulfinyl]amino}-2-(4-fluoro-2-methylphenyl)-N-methyl-4-(2-oxoethyl)-1-piperidinecarboxamide (Intermediate 4, 585 mg, 0.898 mmol) in Acetonitrile (5 mL) was added dropwise at 0° C. The mixture was stirred for 7 hours while the temperature was allowed to increase to 25° C. Saturated aqueous NaHCO3 and EtOAc were added to the reaction mixture and the two phases were separated. The combined organic phases were dried (Na2SO4), and evaporated to dryness. The crude was purified by flash chromatography on silica with SP1 (Biotage) system (from 1:0 to 0:1 Cyclohexane/EtOAc) to give the title compound (542 mg, 0.65 mmol, 72% yield) as a white solid.

Provenance & Evidence