HCID 67015665, compound → HCID 67015694, compound

HRID 1617977Notes

Reaction equation

HRID 1617977 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C@H:8]([OH:24])[CH2:9][CH:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH:5]=[CH:4][N:3]=1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:24])[CH2:9][C@H:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 67015665HCID 67015665, compound

Product 1

HCID 67015694HCID 67015694, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (R)-1-(2-methylpyridin-4-yl)-3-phenyl-3-o-tolylpropan-1-ol (110 mg, 347 mmol), and manganese dioxide (121 mg, 1.39 mmol) in toluene (2 mL) was heated at 90° C. for 3 h, then filtered through diatomaceous earth and concentrated in vacuo. Chromatography (silica gel, 10 g, 10% to 50% ethyl acetate in heptane) produced the title compound (60 mg, 55%). White semisolid, MS (ESI+): m/z=316.3 ([M+H]+).

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4304aea977f446ab59edc1db5128f81
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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