Methane → HCID 59022871, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-bromo-2-fluorobenzonitrile (7.34 g, 36.7 mmols) in dry THF (90 mL) was cooled to −78° C. under a nitrogen atmosphere. A 2M solution of LDA in THF (21.48 mL, 43.0 mmols) was added during 15 mins and the mixture was stirred at −78° C. for 2 h giving a deep blue solution. 1,1-dimethylethyl 4{[methyl(methyloxy)amino]carbonyl}-1-piperidinecarboxylate (12.5 g, 45.9 mmols) in dry THF (45 mL) was added and the reaction mixture was allowed to warm to room temperature and stirred for 16 hrs (overnight). Saturated aqueous ammonium chloride (200 mL) was added followed by ethyl acetate (200 mL). The mixture was treated with charcoal to decolorize, filtered and the organic phase separated. The organic layer was washed with saturated aqueous ammonium chloride and dried over MgSO4. Evaporation of the solvent afforded a green solid (16.8 g). The solid was purified by flash chromatography (Dry loaded onto silica, gradient elution with pentane/ethyl acetate 9:1 v/v to 3:2 v/v) to give the title compound (1.35 g) as a green gum (9%).

Provenance & Evidence