Aluminium lithium hydride → 5-Bromo-2-(piperidin-1-ylmethyl)pyridine

Participants

Reaction Steps

Lithium aluminium hydride in 1M THF (1.858 mL, 1.858 mmol) was cooled to 0° C. 5-bromo-2-(1-piperidinylcarbonyl)pyridine (for a preparation see Intermediate 25) (250 mg, 0.929 mmol) was dissolved in THF (7 mL) and added dropwise to the LiAlH4 under nitrogen and stirred. After addition to the reductant, the solution was warmed to room temperature. After 1 hour the reactions were filtered, washed with EtOAc (3×10 mL) and evaporated to dryness to give a brown/yellow solid (159 mg). This was purified on a 25+S Biotage silica column, eluting with DCM:2M MeOH/NH3 (1:0 to 97:3). Product-containing fractions were evaporated to dryness to give a dark yellow solid (61 mg).

Provenance & Evidence