tert-Butyl 4-formylpiperidine-1-carboxylate → 4-(2-Furo[3,2-c]pyridin-2-ylvinyl)piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

LiHMDS (5.9 mL of a 1.0 M solution in THF, 5.90 mmol) was added dropwise to a stirred suspension of furo[3,2-c]pyridin-2-ylmethyltriphenylphosphonium bromide hydrochloride (Preparation 6, 1.50 g, 2.94 mmol) in anhydrous THF (25 mL) at 0° C. After 45 min, the mixture was treated with 4-formylpiperidine-1-carboxylic acid tert-butyl ester (0.63 g, 2.94 mmol), before being stirred at 20° C. for 16 h. The reaction mixture was diluted with EtOAc (300 mL), before being washed with H2O (2×100 mL) and dried (MgSO4). Filtration, solvent evaporation, and flash chromatography (IH-EtOAc, 1:1) furnished 4-(2-furo[3,2-c]pyridin-2-ylvinyl)piperidine-1-carboxylic acid tert-butyl ester: m/z (ES+)=329.1 [M+H]+. This alkene (830 mg, 2.53 mmol) was dissolved in EtOH (15 mL), then Pd (10% on C, 83 mg, 0.08 mmol) was added. The reaction was stirred under a H2 atmosphere for 16 h, before being filtered through celite. The celite was washed with MeOH, then the combined solutions were concentrated to provide the title compound: RT=2.86 min; m/z (ES+)=331.2 [M+H]+.

Provenance & Evidence