Aluminium lithium hydride → 2-(4-Benzyloxy-5-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine

HRID 1404075노트

반응식

HRID 1404075 반응식
[CH2:1]([O:8][C:9]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([C:19](=O)[C:20]([N:22]([CH3:24])[CH3:23])=O)=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCOCC1>[CH2:1]([O:8][C:9]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([CH2:19][CH2:20][N:22]([CH3:23])[CH3:24])=[CH:12][NH:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 669271792-(4-Benzyloxy-5-fluoro-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

생성물 1

HCID 669270882-(4-Benzyloxy-5-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine수율 80%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

A solution of 1-6a (2.26 g, 6.647 mmol) in dry 1,4-dioxane (30 mL) was added dropwise to a slurry of LiAlH4 (2.52 g, 66.47 mmol) in dry 1,4-dioxane (40 mL) at reflux. The mixture was held at reflux for 1 h. The mixture was then cooled, quenched with ice-water (mixed with NaOH), filtered through Celite, and the filter cake was washed with EtOAc. The filtrate and EtOAc washings were combined and extracted three times with EtOAc. The organic layer was washed with 1 N NaOH and brine, dried over Na2SO4 and concentrated. The resulting residue was purified by column chromatography on silica gel with CH2Cl2 (100%) to 5% NH4OH in CH2Cl2 as eluent to give the product (1-7a) as a brown oil in 80% yield, 1.67 g. 1H NMR (300 MHz, CDCl3-d) δ (ppm) 2.14 (s, 6H). 2.52-2.57 (m, 2H), 2.91-2.97 (m, 2H), 5.25 (s, 2H), 6.92-6.98 (m, 3H), 7.31-7.40 (m, 3H), 7.49-7.52 (m, 2H), 7.97 (br, 1H). APCI [M+1]: 313.1.

후처리

  1. temperatureat reflux
  2. temperatureat reflux for 1 h
  3. temperatureThe mixture was then cooled
  4. customquenched with ice-water (mixed with NaOH)
  5. filtrationfiltered through Celite
  6. washthe filter cake was washed with EtOAc
  7. extractionextracted three times with EtOAc
  8. washThe organic layer was washed with 1 N NaOH and brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customThe resulting residue was purified by column chromatography on silica gel with CH2Cl2 (100%) to 5% NH4OH in CH2Cl2 as eluent

출처 및 근거

ORD 기록
ord-7a972c7ab89242f9ba4b813a54828a83
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912220B2

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