Reaktion #1956944

Reaktionsgleichung

LiOH

ester

(±)-Methyl{(2S*,4R*)-1-[(1R*)-1-(4-benzoylphenyl)-4-methylpentyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate

→

acid

Ausbeute 53.9%

(±)-{(2S*,4R*)-1-[(1R*)-1-(4-Benzoylphenyl)-4-methylpentyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetic acid

Ausbeute 53.9%

Lösungsmittel

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethen quenched with 2N HCl (1 ml)
2. 2
   SonstigeThe mixture was partitioned between EtOAc and H2O
3. 3
   ExtraktionThe aqueous layer was extracted with EtOAc (×2)
4. 4
   WaschenThe combined extracts were washed with brine (×1)
5. 5
   Trocknendried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe residue was purified by chromatography (silica, 2-8% MeOH/DCM)

Vorschrift

A solution of LiOH (10 mg, 0.42 mmol) in water (0.5 ml) was added to a stirred solution of the ester (Step 3, 42 mg, 0.074 mmol) in THF (1 ml) at RT. The reaction was stirred at RT O/N then quenched with 2N HCl (1 ml). The mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (×2). The combined extracts were washed with brine (×1), dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (silica, 2-8% MeOH/DCM) to give the acid (22 mg) as a colourless solid. 1H NMR (400 MHz, CD3OD): δ 0.60-0.70 (1H, m), 0.82-1.02 (7H, m), 1.14-1.24 (1H, m), 1.38-1.49 (2H, m), 1.72-1.75 (1H, m), 1.84-1.95 (4H, m), 2.18-2.20 (2H, m), 2.52 (1H, brt, J 11), 2.82 (1H, brd, J 11), 3.53 (1H, dd, J 9.8, 4.0), 3.87 (1H, brd, J 10), 7.45 (2H, d, J 8.2), 7.52 (2H, t, J 7.6), 7.64 (1H, J 7.4), 7.70-7.80 (8H, m); M/Z (ES+) 552 (MH+).

Quelle