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Trifluoroacetic acid → Oxo-[2-(2-phenethyl-4-phenyl-butyryl)-piperidin-1-yl]-acetic acid methyl ester

HRID 1828062
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1828062
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14](=[O:32])[CH:15]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O)(C)(C)C.F[C:34](F)(F)C(O)=O.C(N(CC)CC)C.Cl[C:48](=[O:52])[C:49]([O-:51])=[O:50]>C(Cl)Cl>[CH3:34][O:51][C:49](=[O:50])[C:48](=[O:52])[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14](=[O:32])[CH:15]([CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 210277722-(2-Phenethyl-4-phenyl-butyryl)-piperidine-1-carboxylic acid tert-butyl esterHCID 21988599Chlorooxoacetate

Produkt 1

HCID 21027768Oxo-[2-(2-phenethyl-4-phenyl-butyryl)-piperidin-1-yl]-acetic acid methyl esterAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 0.24 g (0.55 mmol) of 3 in CH2Cl2 (2 mL) was added dropwise 0.13 mL (1.65 mmol) of trifluoroacetic acid, and the mixture was allowed to stir for 2 hours. The solution was diluted with CH2Cl2 (10 mL) and cooled to 0° C. followed by dropwise addition of 0.3 g (3.00 mmol) of triethylamine. After 5 minutes, to the solution was added dropwise 0.08 g (0.61 mmol) of chlorooxoacetate, and the mixture was stirred for 2 hours. The solution was quenched with H2O and extracted with CH2Cl2 (2×200 mL). The organic phase was dried (MgSO4) and evaporated to a clear oil which was subject to column chromatography (EtOAc/Hexanes, 1:3) to yield 0.19 g (81.9%) of 5 as a clear oil. TLC Rf=0.5 (EtOAc/Hexanes, 1:3)

Aufarbeitung

  1. waitAfter 5 minutes
  2. stirringthe mixture was stirred for 2 hours
  3. customThe solution was quenched with H2O
  4. extractionextracted with CH2Cl2 (2×200 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated to a clear oil which

Quellen und Nachweise

ORD-Eintrag
ord-16ae2730f60c4713b2a137b6e9a2dd34
Quelldatensatz
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07056935B2

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