Pyrindan → 6,7-Dihydro-5H-cyclopenta[b]pyridine 1-oxide

3-Chloroperoxybenzoic acid (11.6 g, 67.1 mmol) was dissolved in EtOAc (70 mL, 6 ml/g). The reaction mixture was stirred for 10 minutes at room temperature, and then cooled to 0° C. 2,3-cyclopentenopyridine was dissolved in EtoAc (25 ml, 5 mL/g) which was added dropwise to reaction mixture over 15 minutes keeping the temperature constant below 10° C. The reaction mixture was stirred overnight at ambient temperature. The reaction mixture was quenched with Sat. NaHCO3 (50 mL). The organic layer was dried over sodium sulfate and filtered. Acqu layer was extracted with DCM (40 mL) twice. The organic layer was dried over sodium sulfate and filtered. Combined organic layer was concentrated in vacuo and purification of the crude material via Isco (0-5% Methanol/DCM) gave rise to the desired 6,7-dihydro-5H-cyclopenta[b]pyridine 1-oxide (1.4 g).

1. temperaturecooled to 0° C
2. additionwas added dropwise to reaction mixture over 15 minutes
3. customthe temperature constant below 10° C
4. stirringThe reaction mixture was stirred overnight at ambient temperature
5. customThe reaction mixture was quenched with Sat. NaHCO3 (50 mL)
6. dry with materialThe organic layer was dried over sodium sulfate
7. filtrationfiltered
8. extractionAcqu layer was extracted with DCM (40 mL) twice
9. dry with materialThe organic layer was dried over sodium sulfate
10. filtrationfiltered
11. concentrationCombined organic layer was concentrated in vacuo and purification of the crude material via Isco (0-5% Methanol/DCM)

ORDレコード

ord-571e3f2e607649c095f4255d3f73ce9e

出典データセット

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09227971B2