Pyridine → HCID 86692829, compound

Participants

Reaction Steps

To a solution of 3-hydroxy-1-(pyridin-2-yl)cyclobutanecarbonitrile (WO 2007/060484)(10.996 g, 63.1 mmol) in dry DCM (100 mL) and pyridine (20.59 mL, 252 mmol), was added (with stirring and cooling in an ice water bath) methane sulfonyl chloride (4.88 mL, 63.1 mmol). The mixture was stirred at RT for 25 hours. The solvent was removed at reduced pressure, and the residue was partitioned between EtOAc and aqueous NaHCO3. The organic phase was washed with aqueous NaHCO3 and was concentrated at reduced pressure. The residue was eluted through a short pad of silica gel (eluent 30%-50% EtOAc/hexane). The solvent was removed, and the resulting oil was crystallized from toluene on dilution with hexane to afford the title compound as a 3:1 mixture of geometrical isomers (assessed by NMR).

Provenance & Evidence