Methyl 2-(allyl(benzyl)amino)acetate → HCID 86729460, compound

Participants

Reaction Steps

To a solution of methyl 2-(allyl(benzyl)amino)acetate (0.76 g, 3.5 mmol, 1.0 eq) in anhydrous THF (50 mL) at 20° C. under N2 was added ClTi(OiPr)3 (3.50 mL, 3.50 mmol, 1.0 eq) followed by cyclopentylmagnesium chloride (7.80 mL, 15.6 mmol, 4.5 eq) dropwise via a syringe pump over 4 h. The reaction mixture was quenched with a little of water and extracted with EtOAc (20 mL×3). The combined organic phases were washed with water followed by brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (1:1 (v/v) PE/EtOAc) to afford the title compound as colorless oil (0.48 g, 73%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 190.2 (M+1); 1H NMR (400 MHz, CDCl3) δ: 0.83 (2H, m), 1.09 (1H, t, J=4.8 Hz), 1.36 (1H, m), 2.57 (2H, m), 2.72 (1H, d, J=8.8 Hz), 3.05 (1H, d, J=8.4 Hz), 3.60 (2H, s), 7.25 (5H, m) ppm.

Provenance & Evidence