Hydrochloric Acid → HCID 68650194, compound

HRID 402276Notes

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-27129b5e10fb4b2085744a98119ebd85
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741943B2

Reaction notes

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