Methanol → HCID 69336713, compound

Participants

Reaction Steps

To a stirred solution of racemic Intermediate 16, one enantiomer being [(1S,2S)-2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hex-1-yl]-methanol I (34.5 g, 101 mmol) in acetone (1330 mL) was added Jones Reagent (104 mL) dropwise with stirring. The orange solution was stirred for another 20 minutes. MeOH (˜10 mL) was added cautiously until the solution turned green. The solvent was removed at reduced pressure and the residue partitioned between water and methylene chloride. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. This material was flash chromatographed on silica using a gradient of 10% to 80% EtOAc/Hexanes to give the title compound (23.0 g, 64% yield) as a yellow solid.

Provenance & Evidence