Sodium Bicarbonate → HCID 67092985, compound

Participants

Reaction Conditions

Reaction Steps

Silica gel (particle size 32-63 μm, 60 mg) was added to a solution of tert-butyl 4-oxo-6-azaspiro[2.5]octane-6-carboxylate (PCT Int. Appl. WO 2009010429; 1000 mg, 4.44 mmol) in 1,2-dichloroethane (1 ml). Then a solution of bis(2-methoxyethyl)aminosulfur trifluoride (3.1 g, 13.3 mmol) in toluene (3.6 ml) was slowly added. The resulting mixture was heated to 70° C. and was then stirred at this temperature for 6 h. Sodium bicarbonate (74.6 mg, 888 μmol), potassium fluoride (258 mg, 4.44 mmol) and methyltrioctylammonium chloride (179 mg, 444 μmol) were added at 70° C. and the mixture was stirred at 70° C. for an additional 15 h. The mixture was cooled to room temperature and was then quenched in 20% aq. ammonium hydroxide solution (10 ml) while the pH was maintained around 8.5. The organic phase was separated, washed with water, and evaporated. Chromatography (SiO2; heptane→heptane/ethyl acetate 4:1) afforded the title compound (852 mg, 78%). White solid, MS: 248.2 (M+H)+.

Provenance & Evidence