Tri-o-tolylphosphine → Ammonia

HRID 1433259노트

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HRID 1433259 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[C@@H:16]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:17][CH2:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:32]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]#[N:43])[CH2:33][CH:34]=[CH2:35].C(N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH3:19].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:35]=[CH:34]/[CH2:33][CH2:32][O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]#[N:43])=[CH:11][C:10]=1[C@@H:16]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:17][CH2:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 24885301(R)-3-(2-benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amineHCID 579331896-(But-3-en-1-yloxy)hexanenitrile

생성물 2

HCID 222AmmoniaHCID 57933174HCID 57933174, 화합물

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

반응 조건

온도
90 °C

실험 절차

(3R)-3-[2-(Benzyloxy)-5-bromophenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (WO9411337, 1.21 g, 2.50 mmol) was dissolved in acetonitrile (8 ml) and 6-(but-3-en-1-yloxy)hexanenitrile (Preparation 23, 708 mg, 4.20 mmol), diisopropylethylamine (0.64 ml, 3.75 mmol), palladium acetate (54 mg, 0.25 mmol) and tri(o-tolyl)phosphine (145 mg, 0.25 mmol) were added. The stirred reaction was heated at 90° C., under a nitrogen atmosphere, for 12 hours, cooled to room temperature and the solvent removed in vacuo. The residue was dissolved in ethyl acetate (50 ml) and washed with saturated aqueous sodium hydrogen carbonate (50 ml), brine (50 ml), dried (magnesium sulphate) and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (95/5/0.5 by volume) to furnish the title compound as an oil, 960 mg.

후처리

  1. customThe stirred reaction
  2. temperaturecooled to room temperature
  3. customthe solvent removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  5. washwashed with saturated aqueous sodium hydrogen carbonate (50 ml), brine (50 ml)
  6. dry with materialdried (magnesium sulphate)
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-98d7851093274cb3a6c420dee092ffe9
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612084B2

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