Isopropanol → 4-chloro-2-isopropoxy-6,7-dihydro-5H-cyclopenta[b]pyridine oxide

To a solution of iso-propanol (0.047 g, 0.79 mmol) in dioxane (3 mL) at rt was added potassium tert-butoxide (0.053 g, 0.47 mmol). The mixture was stirred at rt for 30 min. Then, 2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine 1-oxide (0.100 g, 0.39 mmol) in dioxane (1 mL) was added and the mixture was heated under microwave irradiation to 100° C. for 30 min. After this time, the mixture was diluted with methylene chloride and washed with water. The organic layer were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the title compound (0.079 g, 88%) as a white solid. MW=227.69. 1H NMR (CDCl3, 300 MHz) δ 6.73 (s, 1H), 4.90-4.85 (m, 1H), 3.23 (t, J=7.5 Hz, 2H), 3.00 (t, J=7.5 Hz, 2H), 2.20 (quin, J=7.5 Hz, 2H), 1.44 (d, J=6.0 Hz, 6H); APCI MS m/z 228 [M+H]+.

1. temperaturethe mixture was heated under microwave irradiation to 100° C. for 30 min
2. washwashed with water
3. dry with materialThe organic layer were dried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationthe filtrate was concentrated
6. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

ORD record

ord-26239ae189e14d3eb86160e925eadca7

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221843B2