HCID 69336746, compound → HCID 69336894, compound

HRID 1295370Notes

Reaction equation

HRID 1295370 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]=1

Participants

4

Reactant 2

HCID 69336746HCID 69336746, compoundHCID 131709961Jones' reagent

Product 1

HCID 69336894HCID 69336894, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

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).

Workup

  1. customthe material was triturated
  2. filtrationthen filtered
  3. customto remove the solid
  4. concentrationThe filtrate was concentrated
  5. custompartitioned between water of pH=6 and methylene chloride
  6. washThe organics were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-346dd2d9e4464e55a074180d4c55431d
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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