[Na].N.[C:3]([O:7][C:8](=[O:33])[N:9]([CH3:32])[C@:10]12[CH2:15][C@H:14]1[CH2:13][N:12](S(C1C=CC(C)=CC=1)(=O)=O)[C@H:11]2[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:6])([CH3:5])[CH3:4].[Cl-].[NH4+]>C1COCC1>[C:3]([O:7][C:8](=[O:33])[N:9]([CH3:32])[C@:10]12[CH2:15][C@H:14]1[CH2:13][NH:12][C@H:11]2[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([CH3:6])([CH3:5])[CH3:4]To a flame dried 125 mL rbf equipped with a dry ice condenser was added fresh sodium metal (0.32 g, 14.0 mmol). The flask was immersed in a −78° C. bath and ammonia gas was condensed into the flask until it was about a third full. Racemic Intermediate 11, one enantiomer being methyl-[(1R,2S,5S)-2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl ester (0.62 g, 1.4 mmol) in THF (10 mL) was added to the flask in a thin constant stream and the mixture was stirred for 10 minutes until the reaction was complete. Solid ammonium chloride was added and the reaction was warmed to room temperature. The volatile solvents were allowed to evaporate and the residue was partitioned between 1N NaOH and methylene chloride. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound as an oil (0.40 g, quantitative yield).
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