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

Tetrahydro-4H-pyran-4-one → HCID 69122283, Verbindung

HRID 2064094
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2064094
[ClH:1].[F:2][CH:3]([F:21])[O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:9]=2[CH:20]=1.[O:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(N(CC)CC)C.ClCCCl>[ClH:1].[F:21][CH:3]([F:2])[O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:15][CH2:16][N:17]([CH:25]4[CH2:26][CH2:27][O:22][CH2:23][CH2:24]4)[CH2:18][CH2:19]3)[C:9]=2[CH:20]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57423922HCID 57423922, Verbindung

Produkt 1

HCID 69122283HCID 69122283, VerbindungAusbeute 68,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11
1,2-Dichloroethane
Lösungsmittel
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

6-[(Difluoromethyl)oxy]-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride (D54, 0.3 g) 1,2-dichloroethane (10 ml) and triethylamine (0.5 ml), tetrahydro-4H-pyran-4-one (0.6 g), sodium triacetoxyborohydride (0.6 g) was stirred at room temperature over 3 days. The mixture was poured into sodium bicarbonate solution and extracted with dichloromethane. The organic phase was separated, washed with brine and the solvent was removed and the residue was chromatographed on silica gel eluted with dichloromethane/2M ammonia in methanol 0-10%. The resulting product was dissolved in a mixture of methanol and dichloromethane, treated with 1M hydrogen chloride in ether and the solvent was removed. Recrystallisation from methanol gave the title compound as a white solid (0.26 g). Mass Spectrum 368 M+H+

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. customThe organic phase was separated
  3. washwashed with brine
  4. customthe solvent was removed
  5. customthe residue was chromatographed on silica gel
  6. washeluted with dichloromethane/2M ammonia in methanol 0-10%
  7. dissolutionThe resulting product was dissolved in a mixture of methanol and dichloromethane
  8. additiontreated with 1M hydrogen chloride in ether
  9. customthe solvent was removed
  10. customRecrystallisation from methanol

Quellen und Nachweise

ORD-Eintrag
ord-5b0e0ffdbf4e4ba996af0acf0883fa53
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08288413B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion