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 25, 2.5 g, 10 mmol) in THF (Aldrich, 40 ml) and water (10 ml) at 0° C. The resulting solution was allowed to warm to room temperature and stirred at ambient temperature for 10 hours. RP HPLC purification led to the title compound (2.3 g, 94%). MS (electrospray): 139 (M+1); 1HNMR (CDCl3): δ 4.01 (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