3-Hydroxy-1-N-Cbz-pyrrolidine

40499-83-0

501-53-1

95656-88-5

To a solution of pyrrolidin-3-ol (10.45 g, 120.1 mmol) in dichloromethane (300 mL) were sequentially added benzyl chloroformate (24.6 g, 144 mmol) and triethylamine (24.3 g, 240.2 mmol). The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was removed by concentration under reduced pressure. The residue was dissolved in ethyl acetate (100 mL) and extracted with deionized water (60 mL). The organic layer was separated and washed sequentially with deionized water (60 mL) and saturated aqueous sodium chloride solution (60 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, 2:1, v/v) to afford N-CBZ-3-hydroxypyrrolidine (15.2 g, 57% yield) as a colorless gel. LC-MS (ESI): m/z = 222.1 [M + H]+.