Tri-o-tolylphosphine → Ammonia

HRID 1433259ノート

反応式

HRID 1433259 の反応式
[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

参加物

8

反応物 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

生成物 2

HCID 222AmmoniaHCID 57933174HCID 57933174、化合物

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-98d7851093274cb3a6c420dee092ffe9
出典データセット
uspto-grants-2009_11
特許番号
US07612084B2

反応ノート

読み込み中…