Phenol → HCID 66609159, compound

Participants

Reaction Steps

Di-tert-butyl azodicarboxylate (2.20 g, 9.5 mmol) was added portionwise to a stirred solution of 6,7-dihydro-2-(hydroxymethyl)-oxazolo[5,4-c]pyridine-5(4H)-carboxylic acid ethyl ester (1.80 g, 7.95 mmol), phenol (0.90 g, 9.5 mmol) and triphenylphosphine (2.5 g, 9.5 mmol) in THF (40 mL) at 0° C. The mixture was stirred at room temperature for 20 minutes. The solvent was evaporated in vacuo and the crude product purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 20/80). The desired fractions were collected and evaporated in vacuo. The crude product was dissolved with AcOEt and washed with a 10% solution of NaOH. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 6,7-dihydro-2-(phenoxymethyl)-oxazolo[5,4-c]pyridine-5(4H)-carboxylic acid ethyl ester (2.75 g, quantitative yield) that was used in the next step without further purification. C16H18N2O4 LCMS: Rt 2.43, m/z 303 [M+H]+ (using method, LC-MS Method 6).

Provenance & Evidence