3-(Chloromethyl)-3-methyloxetane → HCID 178490659, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 244A (0.75 g, 2.31 mmol) in N,N-dimethylformamide/tetrahydrofuran (1:4, 20 mL) were added potassium tert-butoxide (0.39 g, 3.46 mmol), tetrabutylammonium iodide (0.09 mg, 0.23 mmol) and commercially available 3-(chloromethyl)-3-methyloxetane (TCI, 0.28 g, 2.31 mmol). The reaction mixture was stirred at 80° C. for 16 hours, cooled, diluted with ethyl acetate (20 mL) and quenched with saturated aqueous NaHCO3 (20 mL). The aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with water (1×25 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.24 (s, 3H), 1.33 (s, 9H), 3.77 (s, 3H), 4.19 (d, J=6.1 Hz, 2H), 4.38 (s, 2H), 4.69 (d, J=6.1 Hz, 2H), 7.10 (d, J=9.2 Hz, 1H), 7.29 (s, 1H), 7.44 (dd, J=9.0, 2.9 Hz, 1H), 7.58 (d, J=2.7 Hz, 1H); MS (ESI+) m/z 409 (M+H)+; Anal. Calculated for C20H25ClN2O3S: C, 58.74; H, 6.16; N, 6.85. Found: C, 58.92; H, 6.04; N, 6.84.

Provenance & Evidence