Methyl morpholine oxide → Tert-butyl 4-oxo-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4'-piperidine]-1'-carboxylate

HRID 1096927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096927
[OH:1][CH:2]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]3[NH:28][C:27](=[O:29])[O:26][N:25]=3)[CH:22]=2)[O:17][C:4]2([CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]2)[CH2:3]1.C[N+]1([O-])CCOCC1>C1COCC1.CC#N.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[O:1]=[C:2]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]3[NH:28][C:27](=[O:29])[O:26][N:25]=3)[CH:22]=2)[O:17][C:4]2([CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]2)[CH2:3]1

Komponenten

5

Edukt 2

HCID 82029Methyl morpholine oxideHCID 136136847Tert-butyl 4-hydroxy-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4'-piperidine]-1'-carboxylate

Produkt 1

HCID 136058068Tert-butyl 4-oxo-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4'-piperidine]-1'-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 22177404Acetonitrile tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1.0 g of tert-butyl 4-hydroxy-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-spiro[chroman-2,4′-piperidine]-1′-carboxylate in 40 ml of THF-CH3CN (1:1) ar rt were added 2.0 g of MS 4A, 435 mg of NMO, and 88 mg of TPAP, and the reaction mixture was stirred at rt overnight. The mixture was filtered through a Celite pad, washed with CHCl3 and CHCl3-MeOH (9:1), and the filtrate was concentrated in reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of hexane-AcOEt (100/0-0/100) as eluent to give the intended compound as a colorless solid.

Aufarbeitung

  1. filtrationThe mixture was filtered through a Celite pad
  2. washwashed with CHCl3 and CHCl3-MeOH (9:1)
  3. concentrationthe filtrate was concentrated in reduced pressure
  4. customThe residue was purified by column chromatography on silica gel using
  5. additiona mixture of hexane-AcOEt (100/0-0/100) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-7d21ce4c32374a4cb9b51f519049497e
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138197B2

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