3-Hydroxypyridine → HCID 67154758, compound

Participants

Reaction Steps

To an ice cold solution of triphenylphosphine (1.66 grams, 6.4 mmol) in dry tetrahydrofuran (7 mL) was added diethyl azodicarboxylate (1.0 mL, 6.4 mmol). The mixture was warmed to room temperature and stirred for 30 minutes. The reaction mixture was cooled to 0° C. and a solution of 3-Hydroxymethyl-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (obtained in step (vii) of preparation 1) (0.9 grams, 4.2 mmol) in dry tetrahydrofuran (7 mL) was added followed by a solution of 3-hydroxypyridine (0.6 grams, 6.4 mmol) in dry tetrahydrofuran (14 mL). The reaction mixture was gradually warmed to room temperature and stirred for 0.16 hours. The volatiles were evaporated under reduced pressure and crude obtained was purified by flash column chromatography using 230-400 mesh silica gel to obtain title compound 0.83 grams as gummy liquid. Yield: 68%.

Provenance & Evidence