Synthesis
A four-necked round-bottomed flask was charged with 9.20 g (242.4 mmol) of lithium aluminum hydride and 100 mL of tetrahydrofuran, and 17.00 g (82.84 mmol) of (3S)-N-benzyl-3-hydroxysuccinimide in tetrahydrofuran (80 mL) was added dropwise at 0-10 C. The mixture was heated to reflux and stirred at this temperature for 6 h. The mixture was cooled to 10-20 C and water (40 mL) and 4N sodium hydroxide solution (10 mL) were added, the mixture was filtered and the resulting filter cake was washed with ethyl acetate (2 x 200 mL). The mother liquor was concentrated in vacuo and the remaining residue was dissolved in ethyl acetate (400 mL) and washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to afford 18.00 g (quantitative yield) of (S)-3-hydroxy-1-benzylpyrrolidine as an oil .
