Diethyl Ether → HCID 178523767, compound

Temperature

0 °C

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.

1. customcarefully quenched at 0° C. by the addition of water (40 ml) in THF (60 ml)
2. temperatureto maintain a mobile suspension
3. additionFinally, 1M sodium hydroxide solution (80 ml) was added at 0° C.
4. customresulting in a yellow solution
5. additioncontaining a colourless suspension
6. filtrationThe reaction was filtered through a Celite® pad (filter material)
7. customto remove inorganic salts
8. washThe Celite® pad/salts were washed with EtOAc (500 ml)
9. additiondiluted with further EtOAc (600 ml)
10. washwashed with saturated brine (600 ml)
11. dry with materialThe organic layer was dried (Na2SO4)
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure until a slurry
14. customwas obtained
15. stirringwas then stirred for 5 minutes
16. filtrationbefore being filtered
17. customto recover a colourless solid
18. washThe solid was washed with isohexane
19. customdried at 35° C. under vacuum

ORD record

ord-14f971f520ba4574a7ad13ce2374b96d

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08835444B2