Borane → HCID 28106109, compound

Participants

Reaction Conditions

Reaction Steps

Isobutyric anhydride (2.034 mL, 12.25 mmol) was added dropwise to a stirred solution of 4-butyl-2-methylaniline (2 g, 12.25 mmol) and triethylamine (3.41 mL, 24.50 mmol) in dichloromethane (DCM) (20 mL) under nitrogen. The solution was stirred for 20 hours and then treated with 2M HCl (75 mL) and stirred for 5 minutes. The reaction mixture was extracted with DCM and the combined organic layers were dried over magnesium sulfate. The magnesium sulfate was filtered and the DCM phase concentrated in vacuo to gave N-(4-butyl-2-methylphenyl)-2-methylpropanamide (2.402 g, 10.29 mmol, 84% yield). A stirred solution of N-(4-butyl-2-methylphenyl)-2-methylpropanamide (2.402 g, 10.29 mmol) in tetrahydrofuran (30 mL) under nitrogen was treated dropwise with 1M borane in tetrahydrofuran (BH3 in THF, 30.9 mL, 30.9 mmol; obtainable from, for example, Aldrich). The solution was heated at 60° C. for 2 hours before being quenched with 2M HCl (18 mL) and stirred for a further 15 minutes. It was then basified with aqueous Na2CO3 and extracted with DCM (2×150 mL). The combined organic phases were then dried over magnesium sulfate and concentrated in vacuo. The sample was loaded in dichloromethane and purified on Biotage Flashmaster II on silica (Si) 100 g using a 0-100% dichloromethane-cyclohexane over 60 mins. The appropriate fractions were combined and evaporated in vacuo to give 1.66 g of the title compound as a colourless liquid.

Provenance & Evidence