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

HRID 2222829노트

반응식

HRID 2222829 반응식
[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

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 11575669Methyl 5-((4-bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoate

생성물 1

HCID 68654758Methyl 8-bromo-1-(4-methoxybenzyl)-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate수율 73.5%

시약·촉매·용매 2

HCID 962Water용매HCID 12021Dimethyl Carbonate용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-05415b67485c410793443d49e8c2bd3c
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07371772B2

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