Isopropyl iodide → (1R)-1-{1-[2-(1-methylethyl)-2H-tetrazol-5-yl]-4-piperidinyl}ethanol

Participants

Reaction Conditions

Reaction Steps

A solution of (1R)-1-[1-(1H-tetrazol-5-yl)-4-piperidinyl]ethanol (256 mg, 1.3 mmol) in DMF (1 mL) and acetone (5 mL) was treated with potassium carbonate (359 mg, 2.59 mmol) at room temperature. After stirring for 15 min, 2-iodopropane (661 mg, 3.89 mmol) was added and the mixture was heated at 50° C. for 3 h. The salt was removed by filtration and washed by EtOAc. After concentration, the crude product was purified by chromatography on a silica gel column using MeOH/CH2Cl2 gradient (2.5% to 12.5%) to give 225 mg (69%) of (1R)-1-{1-[2-(1-methylethyl)-2H-tetrazol-5-yl]-4-piperidinyl}ethanol. 1H NMR (400 MHz, CDCl3): δ 4.85 (septet, 1H, J=6.8 Hz), 4.24-4.07 (m, 2H), 3.63 (quint, 1H, J=6.2 Hz), 2.94-2.81 (m, 2H), 2.00-1.89 (m, 1H), 1.76-1.68 (m, 1H), 1.59 (d, 6H, J=6.8 Hz) 1.53-1.31 (m, 4H), 1.22 (d, 3H, J=6.2 Hz).

Provenance & Evidence