Reaktion #2289923

Reaktionsgleichung

compound 1-2

ethyl trans-4-(4-((2-(3,5-dichloropyridin-4-yl)-2-hydroxyethyl)(4-fluorobenzyl)carbamoyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)cyclohexanecarboxylate

Dess-Martin periodinane

→

compound 1-3

Ausbeute 92.9%

ethyl trans-4-(4-((2-(3,5-dichloropyridin-4-yl)-2-oxoethyl)(4-fluorobenzyl)carbamoyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)cyclohexanecarboxylate

Ausbeute 92.9%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was quenched with NaHCO3 (50 mL, sat. aq.) and Na2S2O3 (50 mL, sat. aq.)
2. 2
   Extraktionextracted with DCM (2×150 mL)
3. 3
   WaschenThe combined organic layers were washed with water (100 mL), brine (100 mL)
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by column chromatography (silica gel, eluent: 10% EtOAc/hexane)

Vorschrift

To a stirred solution of compound 1-2 (9.9 g, 15.6 mmol) in DCM (120 mL) was added Dess-Martin periodinane (21.9 g, 21.9 mmol) in portions, and the mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with NaHCO3 (50 mL, sat. aq.) and Na2S2O3 (50 mL, sat. aq.), then extracted with DCM (2×150 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent: 10% EtOAc/hexane) to yield compound 1-3 (9.12 g, 92%) as a white solid. 1H NMR (CDCl3) rotomers present δ 8.74 and 8.67 (2H, 2×s); 7.85 and 7.79 (1H, 2×s); 7.30-7.26 (1H, m); 7.41-7.37 and 7.22-7.15 (3H, 2×m); 4.73-4.51 (4H, m); 4.27-4.21 (1H, m); 4.07 (2H, q, J=7.2 Hz); 2.50-2.48 (1H, m); 2.06-1.93 (6H, m); 1.59-1.54 (2H, m); 1.18 (3H, t, J=6.9 Hz); LCMS: 629 (M+H)+.

Quelle