Reaktion #1602540

Reaktionsgleichung

ester

(±) Methyl {(2S*,4R*)-1-{(1R*)-4-methyl-1-[6-(trifluoromethyl)pyridin-3-yl]pent-4-en-2-yn-1-yl}-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate

LiOH

HCl

→

acid

Ausbeute 71.0%

(±) {(2S*,4R*)-1-{(1R*)-4-methyl-1-[6-(trifluoromethyl)pyridin-3-yl]pent-4-en-2-yn-1-yl}-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetic acid

Ausbeute 71.0%

Lösungsmittel

THF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc
2. 2
   WaschenThe combined extracts were washed with brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was purified by chromatography (silica, 1-2% MeOH/DCM)

Vorschrift

A solution of the ester from Step 2 (0.146 g, 0.28 mmol) and LiOH (0.133 g, 5.6 mmol) in THF (3 ml) and water (3 ml) was stirred at rt for 16 hrs. The reaction mixture was acidified to pH6 with 2N HCl and extracted with EtOAc. The combined extracts were washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (silica, 1-2% MeOH/DCM) to give the acid (0.101 g, 71%). 1H NMR (360 MHz, CD3OD): δ 1.26-1.38 (1H, m), 1.51 (1H, q, J 12.1), 1.77 (1H, m), 1.90-1.98 (2H, m), 2.03 (3H, s), 2.24 (2H, d, J 6.9), 2.43-2.57 (2H, m), 3.74 (1H, dd, J 2.6, 11.4), 4.70 (1H, s), 5.39 (1H, m), 5.46 (1H, s), 7.70-7.72 (4H, m), 7.80 (1H, d, J 8.2), 8.17 (1H, d, J 8.1), 8.82 (1H, s).

Quelle