HCID 68483642, compound → HCID 59438399, compound

Participants

Reaction Steps

A solution of 333 ul (1.0 mmol) of a 3M ethyl magnesium bromide solution in ether in 4 ml THF was cooled to −70° C. A solution of 124 ul (0.42 mmol) titanium isopropoxide in 0.4 ml THF was added dropwise. The light brown mixture was stirred for 2 minutes. A solution of 122 mg (0.4 mmol) rac-(1-Methyl-6-oxo-3-phenyl-piperidin-3-yl)-carbamic acid ter!-butyl ester (example A.22, step 2) in 2.4 ml THF was added dropwise. The mixture was allowed to warm to room temperature and was stirred for 3 hours. The mixture was cooled in an ice bath and quenched with a 20% ammonium chloride solution. Water and ethyl acetate were added. The white suspension was filtered through a pad of dicalite. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 14 mg (11%) of the title compound as a colorless oil. MS (m/e): 317.2 (M+H).

Provenance & Evidence