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

HRID 515453노트

반응식

HRID 515453 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-5ad442450c9c4bcea98fcd936d3082ce
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108957B2

반응 노트

불러오는 중…