StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triethylamine → HCID 178453895, Verbindung

HRID 331399
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 331399
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9](C3CCNCC3)[C:4]=2[CH:3]=[CH:2]1.[C:16]([O:20][C:21](=[O:32])[NH:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([CH2:29][CH:30]=O)[CH2:25][CH2:24]1)([CH3:19])([CH3:18])[CH3:17].C([N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])C.[C:40](=O)(O)[O-].[Na+]>ClCCl>[C:16]([O:20][C:21](=[O:32])[NH:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([CH2:29][CH2:30][N:35]2[CH2:36][CH2:37][CH2:40][CH2:39][CH:38]2[C:7]2[CH:6]=[CH:5][O:1][C:2]3[C:8]=2[CH:9]=[CH:4][CH:3]=3)[CH2:25][CH2:24]1)([CH3:19])([CH3:18])[CH3:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 679724334-(4-Benzofuranyl)-piperidineHCID 178453924HCID 178453924, Verbindung

Produkt 1

HCID 178453895HCID 178453895, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a stirred solution of 4-(4-benzofuranyl)-piperidine (0.3 g, 1.49 mmol) in dichloromethane (8 ml) was added at room temperature commercially available trans-tert-butyl-4-(2-oxoethyl)-cyclohexylcarbamate (1.71 mg, 6.02 mmol) and triethylamine (0.3 g, 0.42 ml, 2.98 mmol) and the solution was allowed to stir for 30 min. Sodium triacetoxyboron hydride (0.57 g, 2.68 mmol) was added step wise and the mixture was allowed to stir for 16 h at room temperature. The solution was poured into saturated sodium bicarbonate solution (20 ml) and extracted with dichloromethane (2×40 ml). The combined organic layers were washed with saturated sodium bicarbonate solution (20 ml), dried (MgSO4) and evaporated. The crude material (0.77 g) was purified by flash chromatography on silica gel (dichloromethane/MeOH 5-10%) to yield trans-{4-[2-(4-benzofuran-4-yl-piperidin-1-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester as a white solid (0.63 g, 99%), MS (ISP) m/z=427.4 [(M+H)+], mp 133° C.

Aufarbeitung

  1. stirringto stir for 16 h at room temperature
  2. extractionextracted with dichloromethane (2×40 ml)
  3. washThe combined organic layers were washed with saturated sodium bicarbonate solution (20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude material (0.77 g) was purified by flash chromatography on silica gel (dichloromethane/MeOH 5-10%)

Quellen und Nachweise

ORD-Eintrag
ord-31bb30d1cac142f0aec5f453e9e99bef
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877778B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion