2-Fluoroethanol → HCID 86689162, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-acetylamino-5-oxo-4,5-dihydro-pyrazine-2-carboxylic acid methyl ester (300 mg, 1.136 mmol, 80% purity) in dry THF (8 ml) under argon were added triphenylphosphine (119 mg, 0.455 mmol) and diethyl azodicarboxylate (DEAD, 0.072 ml, 0.455 mmol) at −10° C. The reaction was stirred at −10° C. for 15 min and then 2-fluoro-ethanol (0.033 ml, 0.568 mmol) was added. The reaction was stirred at rt for 15 min. To complete the reaction, more triphenylphosphine (119 mg, 0.455 mmol) and DEAD (0.072 ml, 0.455 mmol) were added at −10° C. and the resulting mixture was stirred at −10° C. for 15 min before the addition of 2-fluoro-ethanol (0.033 ml, 0.568 mmol). The reaction was stirred for 100 min. More triphenylphosphine (119 mg, 0.455 mmol) and DEAD (0.072 ml, 0.455 mmol) were added at −10° C. and the resulting mixture was stirred at −10° C. for 15 min before the addition of 2-fluoroethanol (0.033 ml, 0.568 mmol). The reaction was stirred for another 2 h. Saturated aq. NaHCO3 was added and the mixture was extracted with EtOAc, the combined organic layers were washed with aq. sodium chloride, filtered and dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (DCM to DCM/EtOAc 9:1) to provide the title compound as yellow oil (300 mg).

Provenance & Evidence