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Benzyl Alcohol → HCID 60064125, Verbindung

HRID 412606
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 412606
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19]C(O)=O)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:25]([CH2:28]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])C=CC=CC=1.[CH2:47]([OH:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C)C=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:19][NH:25][C:28]([O:54][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:37])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 60064121HCID 60064121, Verbindung

Produkt 1

HCID 60064125HCID 60064125, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 1-tert-butoxycarbonyl-4-ethoxycarbonylpiperidin-4-ylacetic acid (1.6 g) and triethylamine (0.71 ml) in dimethylformamide (20 ml) was added diphenylphosphoryl azide (1.1 ml) at room temperature, and the mixture was stirred at 70° C. for 30 min and then at 90° C. for 10 min. Benzyl alcohol (0.58 ml) was added at the same temperature, and the mixture was stirred for 20 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate and washed with 1N aqueous sodium hydroxide solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography and dried under reduced pressure to give the title compound (1.35 g).

Aufarbeitung

  1. waitat 90° C. for 10 min
  2. stirringthe mixture was stirred for 20 hours
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with 1N aqueous sodium hydroxide solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe obtained residue was purified by silica gel column chromatography
  9. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bba84c346eb84037a3ef2bab2d6c7f3d
Quelldatensatz
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06562828B1

Notizen zur Reaktion

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