Imidazole → HCID 20672301, compound

Participants

Reaction Steps

A solution of 1.57 g (6.0 mmol) of triphenylphosphine and 0.41 g (6.0 mmol) of imidazole in 40 mL of CH2Cl2 was treated with 1.52 g (6.0 mmol) of iodine and stirred at rt for 30 min. A solution of 1.15 g (4.7 mmol) of 2-(S)-((t-butoxycarbonyl)piperidin-4-yl)propanol (from EXAMPLE 30, Step D) in 10 mL of CH2Cl2 was added and the resulting mixture was stirred at rt for 20 h. The reaction mixture was partitioned between 200 mL of ether and 100 mL of H2O and the layers were separated. The organic layer was washed with 100 mL of sat'd NaHCO3, 100 mL of 5% Na2SO3, 100 mL of sat'd NaCl, dried over MgSO4 and concentrated. Flash chromatography on 60 g of silica gel using 10:1 v/v hexanes/ether as the eluant afforded 1.57 g (95%) of the title compound: 1H NMR (500 MHz) δ 0.98 (d, J=6.5, 3H), 1.10-1.20 (m, 2H), 1.26-1.36 (m, 1H), 1.40-1.50 (m, 1H), 1.45 (s, 9H), 1.64 (app d, J=11.0, 11H), 2.67 (br s, 2H), 3.19-3.28 (m, 2H), 4.13 (br s, 2H).

Provenance & Evidence