Methanol → 1,3-Piperidinedicarboxylic acid, 5-methyl-, 1-(1,1-dimethylethyl) ester

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Reaction Conditions

Reaction Steps

136B was dissolved with dioxane (14 mL) and methanol (7 mL). Sodium hydroxide (1.32 g, 33 mmol) in water (2 mL) was added and the mixture was heated to 80° C. for 5 hrs. Solvent was removed under vacuum and the residue was partitioned between 2N HCl (50 mL) and ethyl acetate (50 mL). The mixture was transferred to a separatory funnel and the organics were separated. The aqueous layer was extracted with ethyl acetate (2×25 mL), and the organics were combined and dried over sodium sulfate and filtered. Solvent was removed under vacuum to leave 1-(tert-butoxycarbonyl)-5-methylpiperidine-3-carboxylic acid (136C) as a white solid which was used without further purification. ESI-MS:m/z 266.4 (M+H)+.

Provenance & Evidence