Methanol → 4-(4-Methoxy-benzyl)-6-methyl-[1,4]oxazepane

HRID 515453ノート

反応式

HRID 515453 の反応式
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[CH2:14][CH:13]([CH3:15])[CH2:12][O:11][CH2:10][C:9]2=O)=[CH:5][CH:4]=1.CO.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:14][CH:13]([CH3:15])[CH2:12][O:11][CH2:10][CH2:9]2)=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 667185484-(4-Methoxy-benzyl)-6-methyl-[1,4]oxazepan-3-one

生成物 1

HCID 667188184-(4-Methoxy-benzyl)-6-methyl-[1,4]oxazepane収率 79%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 4-(4-methoxy-benzyl)-6-methyl-[1,4]oxazepan-3-one (4.35 g, 17.5 mmol) in tetrahydrofuran (10.0 ml) was added 1M borane-tetrahydrofuran complex in tetrahydrofuran (52.3 ml, 52.3 mmol) at 0° C. The mixture was stirred at room temperature for 4 hours. After cooling to 0° C., methanol (20 ml) and 6N sodium hydroxide aqueous solution (30 ml) was added carefully. The mixture was refluxed for 2 hours and cooled to room temperature. The organic solvent was removed under reduced pressure. The residue was partitioned between saturated ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant; hexane/ethyl acetate=1/1) to afford 4-(4-methoxy-benzyl)-6-methyl-[1,4]oxazepane as colorless oil (3.24 g, 79%).

後処理

  1. temperatureAfter cooling to 0° C.
  2. temperatureThe mixture was refluxed for 2 hours
  3. temperaturecooled to room temperature
  4. customThe organic solvent was removed under reduced pressure
  5. customThe residue was partitioned between saturated ammonium chloride solution and ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (eluant; hexane/ethyl acetate=1/1)

出典と根拠

ORDレコード
ord-5ad442450c9c4bcea98fcd936d3082ce
出典データセット
uspto-grants-2015_08
特許番号
US09108957B2

反応ノート

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