Water → HCID 69316455, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (60% oil dispersion 11 mg, 0.277 mmol) in tetrahydrofuran (5.0 mL) was added a solution of tert-butyl 4-{[(4-{[trans-2-hydroxycyclopentyl]oxy}-1,2-benzisoxazol-3-yl)oxy]methyl}piperidine-1-carboxylate (80 mg, 0.185 mmol, EXAMPLE 32, Step 1) in tetrahydrofuran (2.0 mL) at 0° C. under nitrogen. After being stirred at 0° C. for 30 min, methyliodide (14 μL, 0.222 mmol) was added to the mixture. The mixture was stirred at 0° C. for 3 h, water was added to the mixture. The mixture was extracted with ethyl acetate (30 mL×2) and washed with brine. The extracts were combined and dried over sodium sulfate and concentrated in vacuo to give an oil. The residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 5:1 to 4:1) to give 78 mg (94%) of the title compound as a colorless viscous oil.

Provenance & Evidence