Potassium Carbonate → Methyl 8-(4-(2-butoxyethoxy)phenyl)-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate

HRID 1810781ノート

反応式

HRID 1810781 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:12][CH2:11][CH2:10][CH2:9][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:7][C:6]=2[CH:17]=1.[CH2:18]([O:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29](OB(O)O)=[CH:28][CH:27]=1)[CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O>[CH2:18]([O:22][CH2:23][CH2:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([C:2]2[CH:3]=[CH:4][C:5]3[NH:12][CH2:11][CH2:10][CH2:9][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:7][C:6]=3[CH:17]=2)=[CH:30][CH:31]=1)[CH2:19][CH2:20][CH3:21]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 230910874-(2-Butoxyethoxy)phenylboric acidHCID 68650133Methyl 8-bromo-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate

生成物 1

HCID 68650013Methyl 8-(4-(2-butoxyethoxy)phenyl)-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate収率 40.1%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒

実験手順

A suspension of methyl 8-bromo-1,2,3,4-terahydro-1-benzoazocine-5-carboxylate (6.0 g), 4-(2-butoxyethoxy)phenyl boric acid (6.26 g) and potassium carbonate (7.28 g) in toluene (100 ml), ethanol (10 ml) and water (10 ml) was stirred under argon atmosphere for 1 hour, after which tetrakis(triphenylphosphin)palladium (1.17 g) was added, and the mixture was refluxed for 6 hours. After returning to room temperature, water was added and the reaction mixture was 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=9:1→hexane:ethyl acetate=4:1), and recrystallized from hexane-ethyl acetate to give methyl 8-(4-(2-butoxyethoxy)phenyl)-1,2,3,4-terahydro-1-benzoazocine-5-carboxylate (3.33 g) as a yellow solid.

後処理

  1. temperaturethe mixture was refluxed for 6 hours
  2. customAfter returning to room temperature
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane ethyl acetate=9:1→hexane:ethyl acetate=4:1)
  8. customrecrystallized from hexane-ethyl acetate

出典と根拠

ORDレコード
ord-a973502d9f2b4c7a9ad1d36178e9b626
出典データセット
uspto-grants-2013_01
特許番号
US08362058B2

反応ノート

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