Triphenylphosphine → Tert-butyl 2-(aminomethyl)-4-chlorobenzylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-azidomethyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzene (10.9 g, 36.73 mmol) in THF (60 mL) and water (6 mL) was added triphenylphospine (10.59 g, 40.40 mmol). The reaction was heated to 50° C. and stirred for 18 h. The reaction was concentrated in vacuo and the residue was purified by flash chromatography using a gradient elution of 2%, 3%, 4%, 5% A in dichloromethane (A=95:5 MeOH:NH4OH). Concentration of product-containing fractions in vacuo gave 2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamine as a solid (8.8 g, 88% yield). TLC Rf=0.3 (95:5:0.25 CH2Cl2:MeOH:NH4OH); HPLC RT=2.64 min (Method A); LC-MS m/z=271; 1H NMR (CDCl3, 400 MHz) 7.21-7.52 ppm (m, 3H); 4.32 ppm (b d, 2H); 3.90 ppm (s, 2H); 1.44 ppm (s, 9H).

Provenance & Evidence