Methyl iodide → Cyclopentanecarboxylic acid, 1-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester

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Reaction Steps

In a 150 mL round-bottomed flask 1-tert-butoxycarbonylamino-cyclopentanecarboxylic acid (1.00 g, 4.36 mmol) was dissolved in acetone (30 mL). Potassium carbonate (1.51 g, 10.9 mmol) was added followed by iodomethane (0.41 mL, 6.54 mmol). The reaction mixture was heated at reflux overnight then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was partitioned between diethyl ether and H2O. The aqueous layer was extracted with diethyl ether. The combined organics were washed with H2O and brine then dried over Na2SO4, filtered and concentrated to afford 1.1 g (99%) of 1-tert-butoxycarbonylamino-cyclopentanecarboxylic acid methyl ester as a white solid.

Provenance & Evidence