Methanol → HCID 86590856, compound

Participants

Reaction Steps

To a solution of (3S)-1-(4-carbamoyl-1,3-thiazol-2-yl)-3-hydroxypyrrolidine (1.42 g, 6.66 mmol) (obtained as described in Reference Example 20(7)) suspended in a mixture of methylene chloride (40 ml) and pyridine (9 ml) were added methanesulfonyl chloride (2.58 ml, 33.3 mmol) and triethylamine (4.67 ml, 33.3 mmol) in an ice bath, and the mixture was stirred for 1 hour. After checking the completion of the reaction, methanol (1.2 ml) was added thereto in an ice bath and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using 5% methanol in ethyl acetate→10% methanol in ethyl acetate as the eluant to afford (3S)-1-(4-carbamoyl-1,3-thiazol-2-yl)-3-methanesulfonyloxypyrrolidine (1.15 g, yield 60%) as a pale yellow solid.

Provenance & Evidence