Nonane → HCID 21906743, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl allyl(methyl)carbamate (0.27 g) in 9-boroabicyclo[3.3.1]nonane (6.24 ml of a 0.5M solution in tetrahydrofuran) was heated at reflux under nitrogen for 4 hours. The solution was cooled to 0° C. and potassium phosphate (1.5 mI of a 3M solution in water) was added. The mixture was stirred for 15 minutes and a solution of N-(1-adamantylmethyl)-2-bromo-5-chloroisonicotinamide (Example 1(ii)) (0.50 g) and dichloro[1,1′-bis(diphenylphosphino)ferrocenyl]palladium (II) (0.045 g) in anhydrous N,N-dimethylformamide (4 ml) was added. The mixture was heated at 60° C. under nitrogen for 3 hours, diluted with saturated brine (25 ml) and extracted into ethyl acetate (3×25 ml). The combined extracts were dried over anhydrous sodium sulphate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with iso-hexane:ethyl acetate (6:1 to 1.5:1). The isolated material (0.50 g) was dissolved in a solution of hydrogen chloride in 1,4-dioxane (10 ml of a 4M solution) and concentrated; the resultant solid was recrystallised from 1,4-dioxane/methanol and the solid collected by is filtration to afford the titled compound (0.19 g) as a colourless powder.

Provenance & Evidence