Hydrogen Bromide → (R)-tert-butyl 2-(4-(pyridin-4-yl)thiazol-2-yl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

A stirred mixture of (R)-tert-butyl 2-carbamothioylpyrrolidine-1-carboxylate (373 mg, 1.6 mmol), 4-(bromoacetyl)pyridine.HBr (455 mg, 1.6 mmol), K2CO3 (224 mg, 1.6 mmol) and EtOH (20 mL) was heated at reflux for 4 h. The mixture was cooled and concentrated. The residues was taken up in EtOAc (90 mL), washed with 0.5 M aq NaoH (20 mL) and brine (20 mL), and dried over Na2SO4. Removal of the solvent left an amber oil (410 mg). A 379-mg portion of the crude product was purified by chromatography on a 12-g silica gel cartridge, eluted with a 0-100% EtOAc in hexanes gradient to afford (R)-tert-butyl 2-(4-(pyridin-4-yl)thiazol-2-yl)pyrrolidine-1-carboxylate (200 mg, 37%) as a tan solid. LC-MS Method 1 tR=1.20 min, m/z=332.

Provenance & Evidence