Aluminium lithium hydride → dibenzyl-[2-(5,7-difluoro-1H-indol-3-yl)-1(S)-methyl-ethyl]-amine

HRID 1272237

반응식

HRID 1272237 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]([CH:22]([CH3:45])[CH:23]([C:25]1[C:33]2[C:28](=[C:29]([F:35])[CH:30]=[C:31]([F:34])[CH:32]=2)[N:27](S(C2C=CC=CC=2)(=O)=O)[CH:26]=1)O)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCOCC1.O1CCCC1>[CH2:15]([N:14]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C@@H:22]([CH3:45])[CH2:23][C:25]1[C:33]2[C:28](=[C:29]([F:35])[CH:30]=[C:31]([F:34])[CH:32]=2)[NH:27][CH:26]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 220148162-(N,N-dibenzylamino)-1-(1-benzenesulfonyl-5,7-difluoro-1H-indol-3-yl)-propan-1-ol

생성물 1

HCID 20806555dibenzyl-[2-(5,7-difluoro-1H-indol-3-yl)-1(S)-methyl-ethyl]-amine수율 93.1%

시약·촉매·용매 1

HCID 22018518Dioxane tetrahydrofuran용매

실험 절차

Lithium aluminum hydride (LAH) (0.7 g, 18 mmol) is added portionwise to a dioxane/tetrahydrofuran (90 ml/10 ml) solution of 2-(N,N-dibenzylamino)-1-(1-benzenesulfonyl-5,7-difluoro-1H-indol-3-yl)-propan-1-ol (1.9 g, 3.3 mmol) under N2 at 0° C. After the addition is complete, the reaction is allowed to warm to room temperature, then is refluxed for 1 hour. The reaction is quenched with H2O and 15% aqueous NaOH, filtered, and the filtrate is diluted with ethyl acetate, washed with brine, dried (Na2SO4), filtered, concentrated, and the residue is purified by flash chromatography (SiO2, ethyl acetate/hexane gradient) to yield 1.2 g of dibenzyl-[2-(5,7-difluoro-1H-indol-3-yl)-1(S)-methyl-ethyl]-amine (86%).

후처리

  1. additionAfter the addition
  2. temperatureis refluxed for 1 hour
  3. customThe reaction is quenched with H2O and 15% aqueous NaOH
  4. filtrationfiltered
  5. additionthe filtrate is diluted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe residue is purified by flash chromatography (SiO2, ethyl acetate/hexane gradient)

출처 및 근거

ORD 기록
ord-0f83313de7e94dc48bcfb74a9f08d9e7
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208505B2

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