Diisopropylamine → HCID 86751250, compound

Participants

Reaction Conditions

Reaction Steps

To an oven dried 50 mL round bottomed flask with a stirring bar, argon inlet and septum was added Boc-isonipecotic acid (2.50 g, 10.90 mmol), 1,1'-carbonyldiimidazole (1.77 g, 10.90 mmol) and dry THF (20 mL). This solution was stirred at 20° C. for 45 min. To a separate, oven dried, 100 mL round bottomed flask with a stirring bar, argon inlet, low temperature thermometer, and septum was added dry THF (30 mL) and distilled diisopropylamine (1.60 mL, 11.45 mmol). This solution was cooled to -78° C. and n-Butyllithium (4.58 mL, of a 2.5M solution in hexane, 11.45 mmol) was added with a syringe. This solution was aged 20 min. then 3-acetylpyridine (1.25 mL, 11.45 mmol) was added dropwise with a syringe. This mixture was stirred for 30 min. at -78° C. then the imidazolide solution was added via a cannula. The mixture was warmed to 20° C. then diluted with EtOAc (350 mL). This solution was washed with 10% aqueous citric acid, saturated aqueous NaHCO3 solution and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave an oil. This material was chromatographed on 120 g of silica gel using 3% 2-propanol in CHCl3 as eluant. 1-(1,1-dimethylethoxycarbonyl)-4-(1-(3-hydroxy-1-oxo-3-(3-pyridinyl)-2-propenyl)piperidine was obtained as an oil.

Provenance & Evidence