N,N'-Dimethylethylenediamine → tert-butyl N-[(3S)-1-(6-chloro-3-fluoro-2-pyridyl)-3-piperidyl]carbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-dichloro-3-fluoro-pyridine (3.802 mmol, 631.1 mg), tert-butyl N-[(3S)-3-piperidyl]carbamate (3.992 mmol; 799.6 mg), potassium carbonate (7.605 mmol; 1051 mg), N,N′-Dimethylethylenediamine (0.3802 mmol; 33.52 mg; 0.0409 mL), and copper(I) iodide; (3.802 mmol; 724.1 mg) in 1,4-Dioxane (15 mL) was purged with Argon then sealed in a pressure tube and heated at 105° C. overnight. The reaction was cooled to room temperature, then filtered through Celite. The filtrate was concentrated and the residue was purified on silica eluted with 0 to 20% EtOAc in Heptane to afford tert-butyl N-[(3S)-1-(6-chloro-3-fluoro-2-pyridyl)-3-piperidyl]carbamate (279.2 mg, 22%) as a white solid.

Provenance & Evidence