2-Bromopyridine → 1-Boc-4-[(2-Bromopyridin-3-yl)hydroxymethyl]piperidine

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) solution of 2-bromo pyridine (800 mg, 5.06 mmol) in freshly distilled THF (15 mL) was added LDA (2.0 M, 2.8 mL, 6.5 mmol). The mixture was stirred under N2 for 30 min. A solution of 4-formyl-piperidine-1-carboxylic acid tert-butyl ester (500 mg, 2.34 mmol) was added slowly to maintain the bath temperature below −70° C. The reaction was stirred at below −70° C. for 30 min, warmed to −20° C. within 60 min, and quenched with saturated aqueous NH4Cl (10 mL). Work-up and purification gave 4-[(2-bromo-pyridin-3-yl)-hydroxy-methyl]-piperidine-1-carboxylic acid tert-butyl ester (470 mg, 50%) as a colourless oil.

Provenance & Evidence