Hydrochloric Acid → Methyl 8-bromo-1-(4-methoxybenzyl)-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate

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Reaktionsgleichung

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[C:4]([CH:26]=O)[CH:3]=1.CO.C[O-].[Na+].Cl>C(=O)(OC)OC.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=3)[CH2:9][CH2:10][CH2:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:26][C:4]=2[CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of methyl 5-((4-bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoate (45.7 g) in dimethyl carbonate (900 ml) was added a methanol solution of sodium methoxide (28%, 26.4 g) and then the mixture was stirred at 50° C. under nitrogen atmosphere for 6 hours. The resultant was cooled to 0° C., followed by addition of water, neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was recrystallized from hexane-ethyl acetate to give methyl 8-bromo-1-(4-methoxybenzyl)-1,2,3,4-terahydro-1-benzoazocine-5-carboxylate (32.2 g) as yellow crystals.

Aufarbeitung

temperatureThe resultant was cooled to 0° C.
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried with magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was recrystallized from hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-05415b67485c410793443d49e8c2bd3c
Quelldatensatz: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07371772B2

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