Hydrochloric Acid → (3S)-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)-3-hydroxypyrrolidine

Participants

Reaction Steps

To a solution of (3S)-3-acetyl-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)pyrrolidine (5.0 g, 17.6 mmol) (obtained as described in Reference Example 20(2)) in ethanol (150 ml) was added sodium ethoxide (60 mg, 0.879 mmol) at room temperature, and the mixture was stirred overnight under the same conditions. After checking the completion of the reaction, a solution of 4N hydrogen chloride in 1,4-dioxane (0.22 ml) was added thereto to neutralize the reaction mixture. 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 obtained residue was purified by chromatography on a silica gel column using toluene:acetonitrile (1:1→1:2) as the eluant to afford (3S)-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)-3-hydroxypyrrolidine (4.16 g, yield 98%) as a white solid.

Provenance & Evidence