Réaction #2487458

Équation de réaction

N-methoxy-N-methylbenzamide

tert-butyl (4-cyclopropyl-2-methylphenyl)carbamate

sec-butyllithium

→

title compound

Rendement 59.5%

tert-Butyl[4-cyclopropyl-2-(2-oxo-2-phenylethyl)phenyl]carbamate

Rendement 59.5%

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was stirred at −45° C. for 35 minutes
2. 2
   workup.STIRRINGstirred at room temperature for 2 more hours
3. 3
   AutreThe reaction mixture was quenched with saturated aqueous ammonium chloride solution/water (2/1, 30 mL)
4. 4
   Extractionfollowed by extraction with ethyl acetate
5. 5
   LavageThe organic layer was washed with saturated brine
6. 6
   Séchagedried over anhydrous sodium sulfate
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   AutreThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Mode opératoire

Under an argon atmosphere, to a solution of tert-butyl (4-cyclopropyl-2-methylphenyl)carbamate (666 mg) in tetrahydrofuran (13.5 mL) was added dropwise sec-butyllithium (1.08 mol/L hexane-cyclohexane solution, 5.5 mL) at −45° C., and the mixture was stirred for 30 minutes. Next, a solution of N-methoxy-N-methylbenzamide (489 mg) in tetrahydrofuran (1.4 mL) was added dropwise thereto, and the mixture was stirred at −45° C. for 35 minutes and then stirred at room temperature for 2 more hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution/water (2/1, 30 mL), followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (563 mg). 1H-NMR (CDCl3) δ ppm: 0.55-0.70 (2H, m), 0.80-1.00 (2H, m), 1.49 (9H, s), 1.75-1.90 (1H, m), 4.25 (2H, s), 6.85-7.00 (2H, m), 7.20-7.75 (5H, m), 8.00-8.15 (2H, m).

Source