Tyramine → HCID 86612125, compound

Participants

Reaction Conditions

Reaction Steps

Tyramine (700 mg, 5.1 mmol) was added to a magnetically stirred suspension of potassium hydride (35 wt. percent dispersion in oil; 876 mg, 7.64 mmol) in DMF (20 mL) at 25° C. After effervescence stopped, tert-butyl 4-fluorobenzoate (1.0 g, 5.1 mmol) was added. After stirring at 25° C. for 64 hours, the reaction was warmed to 60° C. After 48 h, the reaction was poured into brine and extracted with hexanes (3×25 mL) and ethyl acetate (2×25 mL). Organic layers washed separately with aqueous 2 N NaOH, dried (Na2SO4), then pooled, evaporated and purified by silica gel chromatography (CH2Cl2:MeOH/2:1) to provide 0.98 g of clear oil.

Provenance & Evidence