Dichloromethane → (2S)-1-cyclopropanecarbonyl-5-methoxy-2-methyl-1,2,3,4-tetrahydroquinoline

A 1000-mL 3-necked round-bottom flask was charged with (2S)-5-methoxy-2-methyl-1,2,3,4-tetrahydroquinoline (47.41 g, 267.5 mmol), dichloromethane (500 mL), and pyridine (38 mL). Cyclopropanecarbonyl chloride (28.4 g, 271.7 mmol) was added dropwise with stirring at 0° C., and the resulting solution stirred for 3 h at 0° C. The reaction mixture was poured into 400 mL of water/ice, and then washed with 2 N hydrochloric acid (1×100 mL) and brine (3×300 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 0-15% ethyl acetate/petroleum ether) to afford (2S)-1-cyclopropanecarbonyl-5-methoxy-2-methyl-1,2,3,4-tetrahydroquinoline (64.6 g, 98%) as a yellow solid. MS (ES, m/z): 246 [M+H]+

1. stirringthe resulting solution stirred for 3 h at 0° C
2. washwashed with 2 N hydrochloric acid (1×100 mL) and brine (3×300 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated under vacuum
6. customThe residue was purified via column chromatography on silica gel (eluting with 0-15% ethyl acetate/petroleum ether)

ORD 기록

ord-a68cda7ce95546fc8ae4a6568fcb75bd

출처 데이터셋

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09388161B2