Tri-o-tolylphosphine → Ammonia

HRID 1433288ノート

反応式

HRID 1433288 の反応式
[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:23]([O:30][C:31]1[CH:36]=[CH:35][C:34](Br)=[CH:33][C:32]=1[C@@H:38]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH2:39][CH2:40][N:41]([CH:45]([CH3:47])[CH3:46])[CH:42]([CH3:44])[CH3:43])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(C(C)C)CC)(C)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH3:7].[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]/[C:34]2[CH:35]=[CH:36][C:31]([O:30][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:32]([C@@H:38]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH2:39][CH2:40][N:41]([CH:42]([CH3:44])[CH3:43])[CH:45]([CH3:46])[CH3:47])[CH:33]=2)=[CH:12][CH:11]=1)([CH3:3])([CH3:2])[CH3:4]

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 57933209Tert-butyl{2-[4-(pent-4-en-1-yloxy)phenyl]ethyl}carbamate

生成物 2

HCID 222AmmoniaHCID 57933225tert-butyl[2-(4-{[(4E)-5-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}pent-4-en-1-yl]oxy}phenyl)ethyl]carbamate

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

tert-butyl{2-[4-(pent-4-en-1-yloxy)phenyl]ethyl}carbamate (Preparation 56, 1.2 g, 3.9 mmol), (3R)-3-[2-(benzyloxy)-5-bromophenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (Prepared according to WO9411337, 1.9 g, 3.9 mmol), palladium acetate (90 mg, 0.4 mmol), tri(o-tolyl)phosphine (200 mg, 0.8 mmol), and diisopropylethylamine (1.0 ml, 5.9 mmol) were mixed in acetonitrile (12 ml), degassed with argon and the heated to 90° C. for 5 hours. The reaction was cooled to room temperature, filtered through Arbocel and solvent removed in vacuo. The residue was taken up in water and ethyl acetate, the organics were separated, 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 (981210.2 to 95151.5 by volume) to furnish the title compound as a pale yellow foam, 2.5 g.

後処理

  1. customdegassed with argon
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered through Arbocel and solvent
  4. customremoved in vacuo
  5. customethyl acetate, the organics were separated
  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-2582f6eca6a0447492ea662a2073caf8
出典データセット
uspto-grants-2009_11
特許番号
US07612084B2

反応ノート

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