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

HRID 1629707Notes

Reaction equation

HRID 1629707 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:17]=[CH:18][CH:19]=2)[CH:15]=[O:16])[CH2:9][CH3:10])=[CH:4][C:3]=1[CH3:20].[CH3:21][Mg]Br>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:15]([OH:16])[CH3:21])[CH:17]=[CH:18][CH:19]=2)[CH2:9][CH3:10])=[CH:4][C:3]=1[CH3:20]

Participants

4

Reactant 2

HCID 575173193-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-benzaldehydeHCID 178418573HCID 178418573, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of INT 7 (600 mg, 2.09 mmol) in THF (7 mL) at −20° C. was added methylmagnesium bromide (3 M in Et2O, 0.83 mL, 2.50 mmol) dropwise. The reaction mixture was stirred at −20° C. for 1 hour. The mixture was quenched with saturated aqueous NH4Cl and extracted with Et2O (3×). The combined organic layers were washed with brine (2×), dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (heptane/EtOAc) to give INT 10.

Workup

  1. customThe mixture was quenched with saturated aqueous NH4Cl
  2. extractionextracted with Et2O (3×)
  3. washThe combined organic layers were washed with brine (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (heptane/EtOAc)
  8. customto give INT 10

Sources & evidence

ORD record
ord-5439175efe2c4cd7876ec406f3d8b9b0
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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