4-Methylmorpholine → (5-Bromo-3-pyridinyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 12 g (59.4 mmol) of 5-bromopyridine-3-carboxylic acid in 300 mL of anhydrous THF, under argon, are added, at −10° C., 6.6 mL of NMM and then 5.7 mL (59.4 mmol) of ethyl chloroformate. After stirring for 20 minutes at −10° C., 6.8 g (179.8 mmol) of sodium borohydride are added portionwise. The medium is then cooled to −70° C. and 400 mL of MeOH are added over 1 hour 30 minutes. The temperature is then allowed to rise to room temperature and stirring is continued for 12 hours. The medium is then concentrated under reduced pressure and then purified by chromatography on a column of silica gel, eluting with a 98/2 DCM/MeOH mixture. 8.4 g of (5-bromopyridin-3-yl)methanol are obtained in the form of a yellow oil.

Provenance & Evidence