Phosgene → 5-(tert-butyldimethylsilyloxy)-2-phthalimido-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]aniline

HRID 395816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 395816
[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:16]2[C:20](=[O:21])[C:19]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]3[C:17]2=[O:26])=[C:13]([CH:15]=1)[NH2:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:27](Cl)(Cl)=[O:28].[N:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][CH:40]([CH2:43][OH:44])[CH2:39][CH2:38]2)=[CH:33][CH:32]=1>C1(C)C=CC=CC=1.C(Cl)Cl.CCCCCC>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:16]2[C:17](=[O:26])[C:18]3=[CH:25][CH:24]=[CH:23][CH:22]=[C:19]3[C:20]2=[O:21])=[C:13]([CH:15]=1)[NH:14][C:27]([O:44][CH2:43][CH:40]1[CH2:39][CH2:38][N:37]([C:34]2[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=2)[CH2:42][CH2:41]1)=[O:28])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 6371PhosgeneHCID 11310048(1-(Pyridin-4-YL)piperidin-4-YL)methanolHCID 181744945-(Tert-butyldimethylsilyloxy)-2-phthalimidoaniline

Produkt 1

HCID 181745295-(tert-butyldimethylsilyloxy)-2-phthalimido-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]anilineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 5-(tert-butyldimethylsilyloxy)-2-phthalimidoaniline (1.02 g, 2.77 mmol) in toluene (15 mL) was treated with a solution of 20% phosgene in toluene (2 mL) at reflux for 20 min. The volatile materials were removed in vacuo to give a tan solid, which was dissolved in dry methylene chloride (20 mL) and treated with 1-(4-pyridyl)piperidine-4-methanol (0.53 g, 2.77 mmol). The resulting suspension was stirred for 90 min then diluted with hexane. The mixture was allowed to stand overnight and the resulting precipitate collected by vacuum filtration and dried to yield 1.46 g (90%) of the title compound as a tan powder.

Aufarbeitung

  1. temperatureat reflux for 20 min
  2. customThe volatile materials were removed in vacuo
  3. customto give a tan solid, which
  4. waitto stand overnight
  5. filtrationthe resulting precipitate collected by vacuum filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-42475e6d16ee4ec4af2161468ebb36f9
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605626B2

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