Reaction #40674

Reaction equation

Ethyl isonipecotate

triethyl amine

Trimethylacetyl chloride

→

20a

Yield 94.0%

Ethyl 1-pivaloylpiperidine-4-carboxylate

Yield 94.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Temperatureto warm to rt
2. 2
   WashThe reaction mixture was washed with hydrochloric acid solution (1.0 M, aq), sodium bicarbonate (sat., aq.) and sodium chloride (sat., aq.)
3. 3
   DryingThe organic layer dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Otherthe solvent removed

Procedure

Ethyl isonipecotate (20 mL, 130 mmol) was dissolved in 130 mL of dichloromethane and cooled to 0° C. and triethyl amine (19.9 mL, 143 mmol) was added. Trimethylacetyl chloride (16.8 mL, 136 mmol) was added dropwise and the reaction was allowed to warm to rt and stirred for 16 h. The reaction mixture was washed with hydrochloric acid solution (1.0 M, aq), sodium bicarbonate (sat., aq.) and sodium chloride (sat., aq.). The organic layer dried over magnesium sulfate, filtered and the solvent removed to provide 29.5 g (94%) of 20a as a pale orange liquid. LC-MS m/z 242 [M+H]+.

Source