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

HRID 1928939ノート

反応式

HRID 1928939 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 12021Dimethyl Carbonate溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4fef573bcb2e4e95b553a141e5c4c2a2
出典データセット
uspto-grants-2012_05
特許番号
US08183273B2

反応ノート

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