Aluminium lithium hydride → tert-Butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

4-Fluoro-1-(1,1-dimethylethyl)1,4-piperidinedicarboxylic acid-4-ethyl ester (0.40 g, 1.45 mmol) was dissolved in THF (1.5 mL), cooled to 0° C. and treated with lithium aluminum hydride (1 M in THF, 2.90 ml, 2.90 mmol). The reaction mixture was stirred at 0° C. for 2 hours, then warmed to ambient temperature for 3 hours. The reaction was quenched with sequential additions of water (110 μL), 15% NaOH (110 μL), and water (330 μL), and then stirred for 20 minutes. The slurry was diluted with ethyl acetate and filtered. The filtrate was concentrated in vacuo to provide the desired product (0.303 g).

Provenance & Evidence