Morpholine → Tert-butyl 4-(morpholinomethyl)thiazol-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-(hydroxymethyl)thiazol-2-ylcarbamate 89 (2.00 g, 8.68 mmol) was taken up in 25 mL of CH2Cl2 along with Et3N (1.82 mL, 13.05 mmol) and cooled to 0° C. Methanesulfonyl chloride (0.85 mL, 10.88 mmol) was added and the resulting reaction mixture was stirred at 0° C. for 60 min. Morpholine 63 (3.0 mL, 35 mmol) was then added and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure. The resulting residue was taken up in EtOAc and washed with dilute aqueous NaHCO3, brine, dried with Na2SO4, and concentrated under reduced pressure. This material was purified by filtering through a short column of silica gel. The filtrate was concentrated to afford 90 (1.88 g, 69% yield).

Provenance & Evidence