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

HRID 402269Notes

Reaction equation

[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

Participants

Conditions

Temperature: 50 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-bb6c67fed4e64cb6bc612b5bb2704c17
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741943B2

Reaction notes

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