Nitrogen → HCID 131734058, compound

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to an ice-cold solution of tert-butyl 4-(2-ethoxy-2-oxoethyl)-3-fluoropiperidine-1-carboxylate (348 mg, 1.20 mmol) in dry THF (9 mL) was added DIBAL-H (2.41 mL of a 1M solution in toluene, 2.41 mmol). The reaction mixture was stirred at rt for 2 h. DIBAL-H (0.60 mL of a 1M solution in toluene, 0.60 mmol) was added again and the reaction mixture further stirred at rt for 1 h before being cooled to 0° C. Water (0.15 mL) was added followed by aq. 2N NaOH (0.30 mL). The mixture was stirred for 20 min, filtered through celite, washed with EA and concentrated under reduced pressure. The crude residue was purified by FC (hept-EA, 7:3→1:1) to give the title compound as a colorless oil. LC-MS-conditions 08: tR=0.69 min; [M-CH3+H]+=233.35.

Provenance & Evidence