Dimethylformamide → 3-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-benzaldehyde

HRID 1629702Notes

Reaction equation

HRID 1629702 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C@@H:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH3:19])[CH:13]=2)[CH2:10][CH3:11])[CH:5]=[CH:6][CH:7]=1.[Li]C(C)(C)C.CN([CH:28]=[O:29])C>CCOCC>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C@H:9]([NH:8][C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[CH:28]=[O:29])[CH2:10][CH3:11])=[CH:13][C:14]=1[CH3:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 59393853(3-Bromo-phenyl)-[(R)-1-(4-chloro-3-methyl-phenyl)-propyl]-amineHCID 178418306HCID 178418306, compound

Product 1

HCID 575173193-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-benzaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of INT 6 (5.00 g, 14.8 mmol) in Et2O (148 mL) at −78° C. was added tBuLi (1.7 M in pentane, 34.7 mL, 59.0 mmol) dropwise. The mixture was stirred at −78° C. for 40 minutes and DMF (2.5 mL) was added. The reaction mixture was stirred at −78° C. for an additional 30 minutes. The mixture was quenched with saturated aqueous NH4Cl and extracted with Et2O (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (heptane/EtOAc) to afford INT 7.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for an additional 30 minutes
  2. customThe mixture was quenched with saturated aqueous NH4Cl
  3. extractionextracted with Et2O (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (heptane/EtOAc)
  9. customto afford INT 7

Sources & evidence

ORD record
ord-0386c6d7cde2442bb521715b6bf87c8e
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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