N-bromobutanimide → (2S)-6-bromo-1-cyclopropanecarbonyl-2-methyl-1,2,3,4-tetrahydroquinolin-5-ol

HRID 1051557Notes

Reaction equation

[CH:1]1([C:4]([N:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[C:11]([OH:16])[C:10]=3[CH2:9][CH2:8][C@@H:7]2[CH3:17])=[O:5])[CH2:3][CH2:2]1.[Br:18]N1C(=O)CCC1=O>C(#N)C.ClCCl>[Br:18][C:12]1[CH:13]=[CH:14][C:15]2[N:6]([C:4]([CH:1]3[CH2:2][CH2:3]3)=[O:5])[C@@H:7]([CH3:17])[CH2:8][CH2:9][C:10]=2[C:11]=1[OH:16]

Participants

Conditions

Temperature: -10 °C

Procedure

Into a 1000-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed (2S)-1-cyclopropanecarbonyl-2-methyl-1,2,3,4-tetrahydroquinolin-5-ol (4.0 g, 17.3 mmol) in acetonitrile (600 mL) and dichloromethane (150 mL). The solution was cooled to −10° C., and a solution of N-bromosuccinimide (3.08 g, 17.3 mmol) in acetonitrile (50 mL) was added dropwise over 3 h. The resulting solution stirred for 30 minutes at −10° C., and was then concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 0-20% ethyl acetate/petroleum ether) to afford (2S)-6-bromo-1-cyclopropanecarbonyl-2-methyl-1,2,3,4-tetrahydroquinolin-5-ol (3.6 g, 68%) as a light yellow solid. MS: (ES, m/z): 310, 312 [M+H]+

Workup

customInto a 1000-mL 3-necked round-bottom flask purged
temperaturemaintained with an inert atmosphere of nitrogen
concentrationwas then concentrated under vacuum
customThe residue was purified via column chromatography on silica gel (eluting with 0-20% ethyl acetate/petroleum ether)

Sources & evidence

ORD record: ord-d3a18e0db9ad4ae3ab718b6abdb207ac
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388161B2

Reaction notes

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