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

HRID 1051553Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C@H:7]([CH3:13])[NH:8]2.ClCCl.[CH:17]1([C:20](Cl)=[O:21])[CH2:19][CH2:18]1>N1C=CC=CC=1>[CH:17]1([C:20]([N:8]2[C:9]3[C:4](=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][CH:10]=3)[CH2:5][CH2:6][C@@H:7]2[CH3:13])=[O:21])[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 0 °C

Procedure

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]+

Workup

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

Sources & evidence

ORD record: ord-a68cda7ce95546fc8ae4a6568fcb75bd
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388161B2

Reaction notes

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