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Diisopropylamine → methyl (Z)-[4-[3-(4-tert-butylphenyl]-3-[4-[3-(4-hydroxypiperidin-1-yl)propynyl]phenyl]allyloxy]-2-methylphenoxy]-acetate

HRID 1039504
ノート
印刷プレビュー

反応式

HRID 1039504 の反応式
[OH:1][CH:2]1CCN(CC#C)C[CH2:3]1.[CH:11](NC(C)C)(C)C.[C:18]([C:22]1[CH:27]=[CH:26][C:25](/[C:28](/[C:44]2[CH:49]=[CH:48][C:47]([C:50]#[C:51][CH2:52][N:53]3[CH2:58]CO[CH2:55][CH2:54]3)=[CH:46][CH:45]=2)=[CH:29]/[CH2:30][O:31][C:32]2[CH:42]=[CH:41][C:35]([O:36][CH2:37][C:38]([OH:40])=[O:39])=[C:34]([CH3:43])[CH:33]=2)=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]>O1CCCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:18]([C:22]1[CH:27]=[CH:26][C:25](/[C:28](/[C:44]2[CH:49]=[CH:48][C:47]([C:50]#[C:51][CH2:52][N:53]3[CH2:54][CH2:55][CH:2]([OH:1])[CH2:3][CH2:58]3)=[CH:46][CH:45]=2)=[CH:29]/[CH2:30][O:31][C:32]2[CH:42]=[CH:41][C:35]([O:36][CH2:37][C:38]([O:40][CH3:11])=[O:39])=[C:34]([CH3:43])[CH:33]=2)=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 7912DiisopropylamineHCID 186167231-(Prop-2-yn-1-yl)piperidin-4-olHCID 23633559(Z)-[4-[3-(4-tert-Butylphenyl)-3-[4-[3-(morpholin-4-yl)propynyl]phenyl]allyloxy]-2-methylphenoxy]acetic Acid

生成物 1

HCID 86629316methyl (Z)-[4-[3-(4-tert-butylphenyl]-3-[4-[3-(4-hydroxypiperidin-1-yl)propynyl]phenyl]allyloxy]-2-methylphenoxy]-acetate

試薬・触媒・溶媒 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 178418476HCID 178418476、化合物触媒
HCID 8028Tetrahydrofuran溶媒

実験手順

4-Hydroxy-1-propargylpiperidine (171 mg, 1.23 mmol) and diisopropylamine (0.40 mL, 2.85 mmol) were added to a solution of the methyl (Z)-[4-[3-(4-tert-butylphenyl)-3-(4-iodohenyl)llyloxy]-2-methylphenoxy]acetate (350 mg, 0.614 mmol; prepared as described in example 30) in tetrahydrofuran (10 mL). The mixture was degassed and copper(I) iodide (10 mg, 0.053 mmol) and bis(triphenylphosphine)palladium(II) dichloride (22 mg, 0.031 mmol) were added. The reaction mixture was stirred at ambient temperature over night, filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography (silica gel Fluka 60, dichloromethane/methanol 97:3) yielding methyl (Z)-[4-[3-(4-tert-butylphenyl]-3-[4-[3-(4-hydroxypiperidin-1-yl)propynyl]phenyl]allyloxy]-2-methylphenoxy]-acetate as white solid.

後処理

  1. customThe mixture was degassed
  2. filtrationfiltered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by flash column chromatography (silica gel Fluka 60, dichloromethane/methanol 97:3)

出典と根拠

ORDレコード
ord-01218baf8398444bb5cf90b4ba8c591c
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08551993B2

反応ノート

読み込み中…

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