C[O:2][C:3]([C:5]1([CH3:24])[CH:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:8][N:7]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:6]1)=[O:4].O[Li].O>C1COCC1.O.CO>[CH2:17]([N:7]1[CH2:8][CH:9]([C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[C:5]([CH3:24])([C:3]([OH:4])=[O:2])[CH2:6]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1A mixture of 7.7 g (22.4 mmol) rac-(3R,4R)-1-Benzyl-4-(4-chloro-phenyl)-3-methyl-pyrrolidine-3-carboxylic acid methyl ester and 1.41 g (22.4 mmol) LiOH.H2O in 80 mL THF, 80 mL water and 8 mL methanol was heated to reflux over night. The organic solvents were removed under vacuum and the pH was adjusted to 4-5 by addition of HCl aq. (1N). The mixture was extracted with ethyl acetate/THF (2:1) and the combined organic layers were washed with brine, dried with Na2SO4, filtered off and evaporated to dryness. The residue was dried to yield 7.2 g (97%) of the title compound as light brown foam. MS m/e: 328.3 [M+H]+.
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