Triethylborane → HCID 68823743, compound

Participants

Reaction Steps

Triethylborane (1M in THF, 12 mL, 12 mmol) is added to a solution of 5-Methyl-3-oxazol-5-yl-isoxazole (1.8 g, 12 mmol) in 40 mL of dry Tetrahydrofuran and the mixture is stirred at room temperature for 15 minutes. The mixture is cooled to −78° C., nBuLi (2.5M in Hexanes, 4.8 mL, 12 mmol) is added drop wise and the mixture is stirred at −78° C. for 15 minutes. A solution of (S)-1-Formyl-propyl)-carbamic acid tert-butyl ester (898.7 mg, 4.8 mmol) in 15 mL of dry tetrahydrofuran is added drop wise and the reaction mixture is stirred at −78° C. for 3 hours, then let warm to −30° C. and quenched with acetic acid in ethanol (4%, 250 mL), stirring continued for 2 hours, while warming to room temperature. The reaction is concentrated under reduced pressure; the residue is dissolved in diethyl ether (250 mL) and stirred for 1.5 hours at room temperature. The precipitate is filtered; the filtrate is concentrated under reduced pressure. Column chromatography on silica eluting with a mixture of methylene chloride and ethyl acetate gives the title compound as a solid (830 mg).

Provenance & Evidence