Imidazole → HCID 86614566, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl (benzyl{[1-(hydroxymethyl)cyclopropyl]methyl}-amino)acetate (1.1 g, 0.0042 mol), triphenylphosphine (2.74 g, 0.0104 mol) and 1H-imidazole (0.711 g, 0.0104 mol) in ether (30.0 mL, 0.286 mol) and ACN (10.0 mL, 0.192 mol) at 0° C. was added iodine (2.12 g, 0.00835 mol). The resulting yellow suspension was stirred at 0° C. for 50 min. The reaction was quenched by the addition of 10% aqueous Na2S2O3 (30 ml) and saturated aqueous NaHCO3 (30 mL). The product was extracted with EtOAc (2×) and the combined organic extracts were washed with brine, then dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by Combiflash chromatography eluting with 0-15% EtOAc/hexanes to afford the desired product (1.0 g). LC/MS: 374.1 (M+1H)+.

Provenance & Evidence