Sodium borohydride → HCID 66609140, compound

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Reaction Steps

Sodium borohydride (0.71 g, 18.8 mmol) was added to a stirred solution of 2-formyl-6,7-dihydro-oxazolo[5,4-c]pyridine-5(4H)-carboxylic acid ethyl ester (2.82 g, 12.6 mmol) in MeOH (140 mL) at 0° C. The mixture was stirred at room temperature for 20 minutes, diluted with brine and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0 and then MeOH in AcOEt 15/85). The desired fractions were collected and evaporated in vacuo to yield 6,7-dihydro-2-(hydroxymethyl)-oxazolo[5,4-c]pyridine-5(4H)-carboxylic acid ethyl ester (1.8 g, 63% yield) as a colorless oil. C10H14N2O4 LCMS: Rt 0.72, m/z 227 [M+H]+ (using method, LC-MS Method 6).

Provenance & Evidence