(+/-)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropionamide → 3-(2-(Benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine

HRID 131770

반응식

HRID 131770 반응식
[CH:1]([N:4]([CH:30]([CH3:32])[CH3:31])[C:5](=O)[CH2:6][CH:7]([C:14]1[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:15]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1>O1CCCC1>[CH2:22]([O:21][C:15]1[CH:16]=[CH:17][C:18]([Br:20])=[CH:19][C:14]=1[CH:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH:30]([CH3:32])[CH3:31])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

4

반응물 2

HCID 22735207(+/-)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropionamideHCID 68718528lithium aluminium hydride THF

생성물 1

HCID 129724153-(2-(Benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine수율 76.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of (±)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropionamide (11.8 g) in 40 ml of dry tetrahydrofuran was added 1 M lithium aluminium hydride/tetrahydrofuran (36 ml). The reaction was refluxed for 4 hrs and then quenched with the dropwise addition of water. After removal of the precipitate the solvent was evaporated and the oily residue dissolved in diluted sulphuric acid. The aqueous phase was washed several times with diethyl ether, adjusted to pH 10-12 (aqueous NaOH), and extracted with diethyl ether. The extract was dried (sodium sulphate), filtered and evaporated to dryness in vacuum to leave 8.1 g (76.7%) of the title compound as a viscous colourless oil, tlc: (4) 0.86. The NMR spectrum corresponds to the product, obtained from the tosylate precursor (see above).

후처리

  1. temperatureThe reaction was refluxed for 4 hrs
  2. customquenched with the dropwise addition of water
  3. customAfter removal of the precipitate the solvent
  4. customwas evaporated
  5. dissolutionthe oily residue dissolved in diluted sulphuric acid
  6. washThe aqueous phase was washed several times with diethyl ether
  7. extractionextracted with diethyl ether
  8. dry with materialThe extract was dried (sodium sulphate)
  9. filtrationfiltered
  10. customevaporated to dryness in vacuum

출처 및 근거

ORD 기록
ord-ebeab2bbd8ee47d79740856c3333cf9f
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384980B2

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