Aluminium lithium hydride → 2,6-dichloro-N-[(1R)-2-[2-(2,6-dichlorophenyl)-6-quinolinyl]-1-(hydroxymethyl)ethyl]benzamide

Participants

Reaction Conditions

Reaction Steps

To methyl (2R)-2-[(2,6-dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 36 (0,222 g) in THF (1 ml) is added, at 0° C., LiAlH4 (1.5 equ.). The solution is stirred at 0° C. for 1 hour. The reaction is quenched at −25° C. by successive additions of water (25 μl), 15% NaOH (25 μl) and water (75 μl). After evaporation of THF under vacuum, AcOEt is added. The organic phases are washed with water, brine, dried over MgSO4 and evaporated. The resulting residue is purified over silica gel using CH2Cl2/CH3OH/NH4OH (99/1/0.1) as eluent to give 2,6-dichloro-N-[(1R)-2-[2-(2,6-dichlorophenyl)-6-quinolinyl]-1-(hydroxymethyl)ethyl]benzamide 60.

Provenance & Evidence