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

HRID 1096926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096926
[Si]([O:8][CH:9]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:31]3[NH:35][C:34](=[O:36])[O:33][N:32]=3)[CH:29]=2)[O:24][C:11]2([CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[CH2:10]1)(C(C)(C)C)(C)C.C([O-])(O)=O.[Na+]>CCO.C1COCC1>[OH:8][CH:9]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:31]3[NH:35][C:34](=[O:36])[O:33][N:32]=3)[CH:29]=2)[O:24][C:11]2([CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[CH2:10]1

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 136136848HCID 136136848, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21873804Tetrahydrofuran ethanolLösungsmittel

Versuchsvorschrift

To a solution of 13.4 g of tert-butyl 4-([tert-butyl(dimethyl)silyl]oxy)-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-spiro[chroman-2,4′-piperidine]-1′-carboxylate in 200 mL of EtOH-THF (5.5:1) at 0° C. was added 67 ml of 1M HClaq dropwise, and the reaction mixture was stirred at rt for 18 h. The reaction mixture was cooled to 0° C., and the mixture was basified with NaHCO3. The mixture was concentrated in reduced pressure, and the residue was acidified with 1M HClaq. The aqueous mixture was extracted with a mixture of CHCl3-MeOH (9:1) three times, and the combined organic layers was washed with brine, dried over Na2SO4, and concentrated in reduces pressure to give the product as a pale brown solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. concentrationThe mixture was concentrated in reduced pressure
  3. extractionThe aqueous mixture was extracted with a mixture of CHCl3-MeOH (9:1) three times
  4. washthe combined organic layers was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in reduces pressure

Quellen und Nachweise

ORD-Eintrag
ord-f81210f827b54964b30a38b766e45222
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138197B2

Notizen zur Reaktion

Wird geladen…