Triphenylphosphine → 5-Aminomethyl-2-cyanothiophene

Participants

Reaction Steps

Triphenylphosphine (Aldrich, 5.7 g) was added to a solution of 2-cyano-5-(azidomethyl)thiophene (compound 24, 2.5 g, 10 mmol) in THF (Aldrich, 40 mL) and water (10 mL) at 0° C. The solution was allowed to warm to room temperature and stirred at ambient temperature for 10 hours. RP-HPLC purification gave the title compound (2.3 g, 94%). MS (electrospray) 139 (M+1); 1HNMR (CDCl3) δ4.01 (s, 2H), 4.75 (br s, 2H, NH2), 6.82 (d, 1H, J=3.5 Hz), 7.08 (d, 1H, J=3.5 Hz).

Provenance & Evidence