1,1-Dimethylethyl 4-(3-{6-[(2,2-dimethylpropanoyl)amino]-2-fluoro-3-pyridinyl}-3-oxopropyl)-1-piperidinecarboxylate → Tert-butyl 4-[3-(6-amino-2-methoxy-3-pyridinyl)-3-oxopropyl]-1-piperidinecarboxylate

Participants

Reaction Steps

A mixture of 1,1-dimethylethyl 4-(3-{6-[(2,2-dimethylpropanoyl)amino]-2-fluoro-3-pyridinyl}-3-oxopropyl)-1-piperidinecarboxylate (step 2, 360 mg, 0.827 mmol) and potassium tert-butoxide (278 mg, 2.48 mmol) in methanol (8 ml) was refluxed for 1 h. After cooling to room temperature, the mixture was diluted with water (20 ml) and extracted with diethyl ether (100 ml×2). The combined organic layer was washed with water (50 ml) and brine (50 ml), and dried over magnesium sulfate. Removal of the solvent gave 300 mg (100%) of the title compound as a colorless gum.

Provenance & Evidence