Methyl iodide → (S)-tert-butyl 4-(2-(1-methoxycyclopentyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate

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Reaction Steps

The (S)-tert-butyl 4-(2-(1-hydroxycyclopentyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate was added to a suspension of NaH (568 mg, 14.2 mmol, 4.0 equiv) and the mixture stirred for 0.5 h. Methyl iodide (2.106 g, 14.2 mmol, 4.0 equiv) was added and the mixture stirred for 48 h at ambient temperature. The excess NaH was quenched by careful addition of water. The mixture was evaporated, and then taken up in EtOAc. The solution was washed with water, then brine and evaporated. The ether was purified by flash chromatography on silica, eluting with 0-41% EtOAc in hexanes. This afforded 1170 mg (3.4 mmol, 95% yield for two steps) of the desired (S)-tert-butyl 4-(2-(1-methoxycyclopentyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate.

Provenance & Evidence