Imidazole → HCID 86622724, compound

Participants

Reaction Steps

To a mixture of the product of Example 325, Step A (9.8 g, 22.5 mmol), Zn(N3)2/bis-pyridine complex (Synthesis 1990, 130) (13.9 g, 45.1 mmol), triphenylphosphine (11.8 g, 45.1 mmol), and imidazole (6.1 g, 90 mmol) in 100 mL of CH2Cl2 was added diisopropyl azodicarboxylate (8.8 mL, 45.1 mmol) dropwise at rt. The mixture was allowed to stir at rt for 16 h. The supernatant was separated and washed with diluted HCl (1.0 N, 3×50 mL), saturated aq NaHCO3 (3×50 mL) and brine (50 mL). The organic layer was separated, dried over MgSO4, and concentrated. Chromatography on Biotage 40+M cartridges using 3:17 v/v EtOAc/hexanes as the eluant afforded the product: 1H NMR δ 1.47 (s, 3H), 1.59 (s, 3H), 2.11 (dd, J=9.6, 13.5, 1H), 2.32 (dd, J=6.1, 13.6, 1H), 4.75 (dd, J=6.0, 9.6, 1H), 7.04 (d, J=8.5, 2H), 7.19-7.28 (m, 5H), 7.78 (s, 1H).

Provenance & Evidence