Sulfuric Acid → 2-(3-(3,4-Dichlorophenyl)pyrrolidin-3-yl)ethanol

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反応手順

A solution of LiAlH4 (450 mL, 1M in THF, 450 mmol) was cooled in a ice/acetone bath (-10° C.). A solution of H2SO4 (99.999%) (12 mL, 225.3 mmol) in THF (35 mL) was added dropwise. (Use caution when adding the H2SO4 to the THF and also when adding the H2SO4 /THF solution to the LiA1H4) After the addition was complete, the slurry was stirred for 1 h in an ice bath. The slurry was allowed to warm to ambient temperature and stir for 2 h. A solution of [3-(3,4-dichloro-phenyl)-5-oxo-pyrrolidin-3-yl]-acetic acid ethyl ester (23.2 g, 73.4 mmol) in THF (70 mL) was added dropwise. The slurry was heated to 45°-50° C. for 36 h. The slurry was cooled in an ice bath and a solution of THF:H2O (1:1, 70 mL) was added dropwise. The slurry was filtered and the solids were rinsed with THF and dichloromethane. The salts were stirred with THF:H2 0:15% NaOH (1 L :70 mL :20 mL) for 2 h. The slurry was filtered and the combined filtrates were concentrated in vacuo to obtain a residue. The residue was dissolved in dichloromethane and the solution was dried over MgSO4, filtered, and concentrated in vacuo to obtain a residue. The residue was recrystallized from diethyl ether to give the title compound:

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