Sodium hydride → HCID 68539596, compound

Participants

Reaction Conditions

Reaction Steps

5-Methyl-spiro[indoline-3,4′-piperidin]-2-one (prepared as in Org. Prep. Proced. Int. (1995), 27(6), 691-694)(0.05 g, 0.023 mmol) was dissolved in dry N,N-dimethylformamide (4.0 mL). To the reaction mixture was then added at 0° C. sodium hydride (60% in mineral oil, 10.0 mg, 0.28 mmol) under nitrogen atmosphere and the reaction mixture was stirred at 0° C. for one hour. To the reaction mixture was then added at 0° C. 2-(2-bromo-ethoxy)-tetrahydro-pyran (0.048 g, 0.023 mmol). The reaction mixture was stirred at 0° C. for 1 hour, then at room temperature under nitrogen atmosphere for 18 hours. The reaction mixture was then partitioned between water-ice and ethyl acetate. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield the title compound as a crude oil. The crude oil was purified via flash chromatography (3% methanol/dichloromethane) to yield the title compound as an oil.

Provenance & Evidence