Reaktion #2289922

Reaktionsgleichung

compound 1-1

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

TBAF

→

compound 1-2

Ausbeute 84.0%

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

Ausbeute 84.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm up from 0° C. to room temperature
2. 2
   SonstigeThe reaction mixture was quenched with saturated aqueous NH4Cl (100 mL)
3. 3
   Extraktionextracted with EtOAc (2×150 mL)
4. 4
   WaschenThe combined organic layers were washed with water (100 mL), brine (100 mL)
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe residue was purified by column chromatography (silica gel, eluent: 70% EtOAc/hexane)

Vorschrift

To a stirred solution of compound 1-1 (15 g, 20.2 mmol) in THF (20 mL) was added TBAF (1.0 M in THF, 40.4 mL, 40.4 mmol) dropwise at 0° C., and the mixture was allowed to warm up from 0° C. to room temperature while stirred for 2 h. The reaction mixture was quenched with saturated aqueous NH4Cl (100 mL) and extracted with EtOAc (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: 70% EtOAc/hexane) to provide compound 1-2 (9.9 g, 84% over two steps) as a yellow-brown gum. 1H NMR (CDCl3) rotomers present δ 8.42 and 8.38 (2H, 2×s); 7.57 and 7.53 (1H, 2×s); 7.41-7.35 and 7.14-7.09 (4H, 2×m); 5.61-5.45 (1H, m); 5.10-4.50 (3H, m); 4.25-3.90 (4H, m); 3.31-3.15 (1H, m); 2.23-2.16 (6H, m); 1.65-1.51 (2H, m); 1.28-1.23 (3H, m); LCMS: 631 (M+H)+.

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