Sodium Hydroxide → HCID 54403008, compound

Participants

Reaction Steps

Under nitrogen atmosphere to a solution of potassium tert-butoxide (17.0 g) in N,N-dimethylformamide (77 ml) was slowly dropped thioacetic acid (12.1 g) at 0° to 10° C., and then the solution was stirred for 30 minutes at the same temperature. This solution was added to a solution of (2R,4R)-1-allyloxycarbonyl-4-methanesulfonyloxy-2-(pyrimidin-5-ylmethyl) pyrrolidine (25.8 g) in N,N-dimethylformamide (154 ml) at 15° to 25° C. under nitrogen atmosphere, and the reaction mixture was stirred for 2 hours at 80° to 90° C. After the reaction mixture was cooled and poured into ice-water (500 ml) and ethyl acetate (300 ml), the aqueous layer was adjusted to pH 8.2 with 1N-sodium hydroxide. The organic layer was separated and washed with water containing 10% sodium chloride (300 ml). This fraction and the fraction reextracted from the aqueous layer were combined, dried over magnesium sulfate, and evaporated under reduced pressure to give an oil. The oil was dissolved in toluene (300 ml) and it was washed with water (150 ml), dried over magnesium sulfate and then evaporated. The residue was subjected to column chromatography on silica gel (250 g) (solvent; hexane:ethyl acetate=3:1 to 1:6) to give (2R,4S)-4-acetylthio-1-allyloxycarbonyl-2-(pyrimidin-5-ylmethyl) pyrrolidine (17.7 g) as an oil.

Provenance & Evidence