2-Bromoethyl methyl ether → 4-(2-Methoxy-ethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

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Reaction Conditions

Reaction Steps

To a solution of 38 mL (76 mmol) LDA in THF (2N) was added 9.8 g (38 mmol) 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (commercially available) in 10 mL THF at −5° C. and stirred at −5° C. for 3 h. 10.58 g (76 mmol) 1-bromo-2-methoxyethane in 10 mL THF was added drop-wise, stirred for 1 h at −5° C. and stirred at room temperature over night. KHSO4 aq. (1M) was added and the mixture was extracted with ethyl acetate. The combined organic layers were dried with MgSO4 and evaporated to dryness. The residue was purified by column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane to yield after evaporation of the product containing fractions 8.19 g (68%) of the title compound as yellow oil. MS m/e: 315.2 [M+H]+.

Provenance & Evidence