1-{3-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-phenyl}-ethanol → 1-{3-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-phenyl}-ethanone

HRID 1629708Notes

Reaction equation

HRID 1629708 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:18]([OH:20])[CH3:19])[CH:15]=[CH:16][CH:17]=2)[CH2:9][CH3:10])=[CH:4][C:3]=1[CH3:21]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11][C:12]2[CH:13]=[C:14]([C:18](=[O:20])[CH3:19])[CH:15]=[CH:16][CH:17]=2)[CH2:9][CH3:10])=[CH:4][C:3]=1[CH3:21]

Participants

3

Reactant 1

HCID 673448641-{3-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-phenyl}-ethanol

Product 1

HCID 575173211-{3-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-phenyl}-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of INT 10 (446 mg, 1.47 mmol) in CH2Cl2 was added DMP (747 mg, 1.76 mmol). The reaction mixture was stirred at room temperature for 1 hour. The mixture was quenched with saturated aqueous NaHCO3/saturated aqueous Na2S2O3 5/1 and diluted with CH2Cl2. The mixture was stirred vigorously until the organic layer was clear. The organic layer was washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (heptane/CH2Cl2) to afford INT 11.

Workup

  1. customThe mixture was quenched with saturated aqueous NaHCO3/saturated aqueous Na2S2O3 5/1
  2. additiondiluted with CH2Cl2
  3. stirringThe mixture was stirred vigorously until the organic layer
  4. washThe organic layer was washed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (heptane/CH2Cl2)
  9. customto afford INT 11

Sources & evidence

ORD record
ord-646bcce9561644a9867ace059a483b11
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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