Iodoethane → HCID 66973612, compound

Participants

Reaction Conditions

Reaction Steps

To a 1 M solution of sodium bis(trimethylsilyl)amide in THF (1.64 mL, 1.64 mmol) at −78° C. was added dropwise a solution of tert-butyl (2R,5R)-2-ethyl-3-oxo-5-phenylmorpholine-4-carboxylate from Step C (500 mg, 1.64 mmol) in DME (25 mL) at −78° C. The resulting mixture was stirred at −78° C. for 10 min then iodoethane (0.131 mL, 1.64 mmol) was added. After stirring at −78° C. for 30 min, then at −30° C. for 30 min, the reaction mixture was cooled to −78° C. and quenched with saturated aqueous NH4Cl (20 mL) then extracted with EtOAc (2×40 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—95:5 to 70:30, to give the title compound. MS: m/z=278 (M−C4H7).

Provenance & Evidence