C([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:9]1)C1C=CC=CC=1.[ClH:18].[H][H]>[C].[Pd].C(O)C>[ClH:18].[CH3:17][S:14]([O:13][C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)(=[O:16])=[O:15]A mixed solution obtained by mixing 2.3 g of 100% pure (S)-1-benzyl-3-methanesulfonyloxypyrrolidine with 3.0 ml of ethanol and adding dropwise 1.00 ml of 35% aqueous hydrochloric acid thereto with cooling on an ice-water bath was charged, together with 300 mg of moist 5% palladium-carbon (water content 52% by weight), into an autoclave, hydrogen was introduced thereinto and the autoclave was heated to raise the temperature to 60 and the pressure to 203 kPa, and the reaction was allowed to proceed for 4 hours. Hydrogen absorption came to an end in 3.2 hours after the start of hydrogen introduction. After completion of the reaction, the reaction mixture was cooled to room temperature and depressurized. The reaction mixture was taken out, the catalyst was filtered off, and the filtrate obtained was concentrated under reduced pressure and further dried under vacuum to give 2.4 g (yield: 84 mole percent) of (S)-3-methanesulfonyloxypyrrolidine hydrochloride.
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