Hexane → 8-Bromo-6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinoline

HRID 1582079Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:16]([CH3:18])[CH3:17])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH3:13])[CH2:9][CH2:8][C:7]2([CH3:15])[CH3:14].[CH2:19]([Li])CCC.CCCCCC>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:16]([CH3:17])[CH3:18])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][CH3:19])[CH2:9][CH2:8][C:7]2([CH3:15])[CH3:14]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 8-bromo-6-isopropyl-4,4-dimethyl-1-ethyl-1,2,3,4-tetrahydro-quinoline (Intermediate 5, 6.81 g, 24.9 mmol), and 150 ml of anhydrous THF under argon at −78° C. was slowly added 1.6 M solution of n-butyl lithium and hexane (33 ml, 52.4 mmol). The reaction mixture was stirred at −78° C. for 10 minutes and thereafter N,N-cirmethylformamide (8.0 ml, 100 mmol) was added. The resulting reaction mixture was stirred at −78° C. for 15 minutes and then quenched with saturated NH4Cl. The product was extracted with diethyl ether. The organic layer was washed with water and brine, dried over Na2SO4, concentrated in vacuo and purified by column chromatography (silica, using 5% ethyl acetate in hexane) to give the title compound as a yellow oil.

Workup

customat −78° C.
additionN,N-cirmethylformamide (8.0 ml, 100 mmol) was added
customThe resulting reaction mixture
stirringwas stirred at −78° C. for 15 minutes
customquenched with saturated NH4Cl
extractionThe product was extracted with diethyl ether
washThe organic layer was washed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
custompurified by column chromatography (silica, using 5% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-2ebdf4eb6b194daabe552eb877746386
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734193B1

Reaction notes

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