Methanol → HCID 69336713, compound

HRID 1295375Notes

Reaction equation

HRID 1295375 reaction equation
[C:1]1([C@@H:7]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH2:11][CH:10]3[C@@:8]2([CH2:23][OH:24])[CH2:9]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)=[O:27].OS(O)(=O)=O.O=[Cr](=O)=O.CO>CC(C)=O>[C:1]1([C@@H:7]2[N:12]([S:13]([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)(=[O:14])=[O:15])[CH2:11][CH:10]3[C@@:8]2([C:23]([OH:27])=[O:24])[CH2:9]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 69346869HCID 69346869, compoundHCID 131709961Jones' reagent

Product 1

HCID 69336713HCID 69336713, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  1. stirringThe orange solution was stirred for another 20 minutes
  2. customThe solvent was removed at reduced pressure
  3. customthe residue partitioned between water and methylene chloride
  4. washThe organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica using a gradient of 10% to 80% EtOAc/Hexanes

Sources & evidence

ORD record
ord-ff33f54b5dcb4dcba1e3cfc214ece66a
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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