2-(3-methoxyphenyl)-2-methylpropan-1-amine synthesis

Yield:-

Reaction Conditions:

Stage #1: 2-(3'-Methoxyphenyl)-2-methylpropionitrilewith borane-THF in tetrahydrofuran at 0 - 20; for 1 h;
Stage #2: with methanol in tetrahydrofuran at 0;

Steps:

147.B; B

A solution of borane in THF (80 mL, 1 M) was added dropwise to a solution of 2-(3- methoxyphenyl)-2-methylpropanenitrile (147a) (2.8 g, 16 mmol) in anhydrous THF (10 mL) at 0⁰C (ice bath). The mixture was allowed to warm up to rt, stirred for 1 hour, and cooled back to O⁰C. MeOH was slowly added until gas evolution ceased. The solution was concentrated and the resulting oily residue was added to IN HCl (60 mL). It was extracted with ethyl acetate (2x 10 mL), and the aquous layer was basified to pH 11 with 3N aqueous NaOH. The aquous was extracted with 10% MeOH/CHCl₃ (3x20 mL). The MeOH/CHCl₃ extracts were combined, dried (MgSO₄), and filtrated. The solvents were removed to afford 147b as a pale yellow oil. MS calcd. for [M+H]⁺ C_MH_I7NO: 180.1; found: 180.1.

References:

WO2008/97428,2008,A2 Location in patent:Page/Page column 114; 115