Hydrochloric Acid → HCID 68650194, compound

HRID 1928946Notes

Reaction equation

CO.C[O-].[Na+].[Br:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([N:14]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH:32]=O)[CH:8]=1.Cl>C(=O)(OC)OC.O>[Br:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]2[N:14]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[CH2:15][CH2:16][CH2:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:32][C:9]=2[CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A methanol solution of sodium methoxide (28%, 1.9 g) was added to a solution of methyl 5-((4-bromo-2-formyl-5-methylphenyl)(4-methoxybenzyl)amino)pentanoate (3.4 g) in dimethyl carbonate (50 ml), after which the mixture was stirred under nitrogen atmosphere at 50° C. for 3 hours. After cooling down to 0° C., water was added and the mixture was neutralized with 1N hydrochloric acid, and then 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 purified by silica gel column chromatography (hexane ethyl acetate=8:1) to give methyl 8-bromo-1-(4-methoxybenzyl)-9-methyl-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate (2.42 g) as a brown oily material.

Workup

temperatureAfter cooling down 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 purified by silica gel column chromatography (hexane ethyl acetate=8:1)

Sources & evidence

ORD record: ord-f7c31b4cf4f74f1b9b370fe4c98eb333
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183273B2

Reaction notes

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