[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1(S)-1-Benzyl-3-hydroxypyrrolidine (1003.5 g, 5.66 mol) was dissolved in toluene (12 L) and the solution stirred and cooled to 0°-5° C. Triethylamine (680 g, 6.67 mol) was added followed by methanesulfonyl chloride (760 g, 6.63 mol) over a 4 hour period. A slurry formed after 30 minutes. The mixture was allowed to stir an additional 1.5 hours and 7% sodium bicarbonate (12 L) was added to the reaction mixture and the organic layer separated. The aqueous layer was extracted with toluene (4 L and 2 L) and the combined organic layers washed with saturated sodium bicarbonate (3×6 L), dried over MgSO4 and concentrated under reduced pressure to give (S)-1-benzyl-3-mesyloxypyrrolidine as a yellow oil (1.41 kg, 98%):
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