4-Toluenesulfonyl chloride → (+/-)-(trans)-Benzyl 3-methyl-4-(tosyloxy)pyrrolidine-1-carboxylate
Reaction equation
[OH:1][C@H:2]1[C@H:6]([CH3:7])[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1.[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>N1C=CC=CC=1>[CH3:7][C@H:6]1[C@H:2]([O:1][S:18]([C:21]2[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:3][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:5]1Participants
4
Procedure
(+/−)-(trans)-benzyl 3-hydroxy-4-methylpyrrolidine-1-carboxylate (9.2 g, 39.1 mmol) in pyridine (50 mL) at 5° C. was added tosyl chloride (9.69 g, 50.8 mmol) in one portion and the resulting mixture was allowed to warm to rt and stir overnight. The reaction mixture was concentrated and the residue was taken up in dichloromethane (400 mL) and washed with water (50 mL×2), 0.5 N HCl (50 mL×2), water, sat aq. sodium bicarbonate (50 mL×2), brine, then dried over magnesium sulfate, filtered and concentrated to give a dark oil as the crude title compound which was used directly without any further purification. HPLC (method B) retention time=3.60 min. LCMS (m+1)=390.