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Tributylphosphine → 2-(4-Fluorophenyl)-1-[4-(1-methylpyrrolidin-3-yloxy)benzyl]-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

HRID 2304679
ノート
印刷プレビュー

反応式

HRID 2304679 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]=3)[CH:9]2[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=[CH:4][CH:3]=1.[CH3:34][N:35]1[CH2:39][CH2:38][CH:37](O)[CH2:36]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1.C(=O)(O)[O-].[Na+].C(Cl)Cl.CO.ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]=3)[CH:9]2[CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][CH:37]3[CH2:38][CH2:39][N:35]([CH3:34])[CH2:36]3)=[CH:31][CH:32]=2)=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 930741-Methyl-3-pyrrolidinolHCID 234407672-(4-Fluorophenyl)-1-(4-hydroxybenzyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

生成物 1

HCID 234408322-(4-Fluorophenyl)-1-[4-(1-methylpyrrolidin-3-yloxy)benzyl]-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline収率 56.3%

試薬・触媒・溶媒 4

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

To a solution of 2-(4-fluorophenyl)-1-(4-hydroxybenzyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline (0.450 g, 1.02 mmol) in THF (5 ml) was added 1-methyl-3-pyrrolidinol (0.22 ml, 2.04 mmol), tri-n-butyl-phosphine (0.5 ml, 2.04 mmol) and 1,1′ azodicarbonyl dipiperidine (0.5 g, 2.04 mmol) respectively. Dichloromethane (4 ml) was added and the reaction was allowed to stir overnight. The reaction was diluted with aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried with MgSO4, filtered and concentrated. The product was purified by radial chromatography (100% CH2Cl2, then CH2Cl2/MeOH, 95:5) to yield the title compound (0.30 g, 56% yield): ES-MS (m/z) 523 [M+H]+.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by radial chromatography (100% CH2Cl2

出典と根拠

ORDレコード
ord-b36cd5b6150747c19d369bb73a8d8ce5
出典データセット
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06436923B1

反応ノート

読み込み中…

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