3-cyclohexyl-N-methoxy-N-methylpropanamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Cyclohexyl-N-methoxy-N-methylpropaneamide (100 mg, 0.502 mmol) obtained in step 1 was dissolved in THF (1.0 mL). Under ice-cooled condition, cyclopropylmagnesium bromide (0.5 mol/L THF solution) (1.20 mL, 0.600 mmol) was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was extracted with ethyl acetate after adding a saturated ammonium chloride aqueous solution. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→80/20) to give 3-cyclohexyl-1-cyclopropylpropan-1-one (61.7 mg, yield 68%). was added The reaction mixture was extracted with ethyl acetate after adding a saturated ammonium chloride aqueous solution The organic layer was washed with saturated brine dried over anhydrous magnesium sulfate The solvent was then evaporated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→80/20)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Cyclohexylpropionic chloride (1.00 g, 5.71 mmol) was dissolved in dichloromethane (10 mL). Under ice-cooled condition, pyridine (0.910 mL, 11.3 mmol) and N,O-dimethylhydroxylamine hydrochloride (840 mg, 8.57 mmol) were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was extracted with ethyl acetate after adding a saturated sodium hydrogen carbonate aqueous solution. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→80/20) to give 3-cyclohexyl-N-methoxy-N-methylpropaneamide (1.13 g, yield 99%). were added The reaction mixture was extracted with ethyl acetate after adding a saturated sodium hydrogen carbonate aqueous solution The organic layer was washed with saturated brine dried over anhydrous magnesium sulfate The solvent was then evaporated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→80/20)