HCID 69336746, compound → HCID 69336894, compound
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[C@@:10]([CH2:14][OH:15])([CH2:11]2)[C@@H:9]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:24].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH2:1]([N:8]1[CH2:13][CH:12]2[C@@:10]([C:14]([OH:24])=[O:15])([CH2:11]2)[C@@H:9]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of racemic Intermediate 38, one enantiomer being ((1S,2S)-3-benzyl-2-phenyl-3-aza-bicyclo[3.1.0]hex-1-yl)-methanol (0.69 g, 2.5 mmol) in acetone (20 mL) was added Jones Reagent (3 mL) dropwise with stirring. Additional acetone (50 mL) was added and the material was triturated then filtered to remove the solid. The filtrate was concentrated and partitioned between water of pH=6 and methylene chloride. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound (0.45 g, 62% yield).