Reaktion #305315

Reaktionsgleichung

2,2,2-trifluoroethanesulfonyl chloride

(S)-2,2-dimethyl-3-(1-methyl-1H-indazol-5-yl)-3-phenylpropanenitrile

lithium aluminum hydride

diethyl ether

→

(S)—N-(2,2-dimethyl-3-(1-methyl-1H-indazol-5-yl)-3-phenylpropyl)-3,3,3-trifluoropropanamide

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture was carefully quenched with MeOH
2. 2
   workup.ADDITIONpoured into brine
3. 3
   Extraktionextracted with ethyl acetate (2×100 mL)
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated

Vorschrift

(a)(b) To a stirred solution of (S)-2,2-dimethyl-3-(1-methyl-1H-indazol-5-yl)-3-phenylpropanenitrile (40 mg, 0.138 mmol) in anhydrous THF (10 mL) was added 1.0M lithium aluminum hydride in diethyl ether (0.5 mL, 0.5 mmol) portionwise at RT under nitrogen. After stirring at RT for 3 hr, the mixture was carefully quenched with MeOH, poured into brine, extracted with ethyl acetate (2×100 mL), dried (MgSO4) and concentrated. The crude product was coupled with 2,2,2-trifluoroethanesulfonyl chloride (26 mg, 0.14 mmol) using General Coupling Method B to give (S)—N-(2,2-dimethyl-3-(1-methyl-1H-indazol-5-yl)-3-phenylpropyl)-3,3,3-trifluoropropanamide. MS found: (M+H)+=426.

Quelle