Diethyl Ether → HCID 178523767, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of trans-4-(2-chloro-5-trifluoromethyl-benzoylamino)-cyclohexane carboxylic acid methyl ester (step 1) (95.2 g, 0.26 mol) in dry THF (1000 ml) under nitrogen at 0° C. was added lithium aluminium hydride pellets (20 g, 0.53 mol) portion wise over 3 hours. The reaction mixture was stirred at 0° C. for a further 2 hours and then carefully quenched at 0° C. by the addition of water (40 ml) in THF (60 ml) followed by further THF (500 ml) to maintain a mobile suspension. Finally, 1M sodium hydroxide solution (80 ml) was added at 0° C. resulting in a yellow solution containing a colourless suspension. The reaction was filtered through a Celite® pad (filter material) to remove inorganic salts. The Celite® pad/salts were washed with EtOAc (500 ml) then with EtOAc:THF (1:1; 300 ml). The organics were combined and diluted with further EtOAc (600 ml) and then washed with saturated brine (600 ml). The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure until a slurry was obtained. Et2O was added to the slurry, which was then stirred for 5 minutes before being filtered to recover a colourless solid. The solid was washed with isohexane and then dried at 35° C. under vacuum to give the required product.

Provenance & Evidence