Ammonium Chloride → Tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

HRID 2300176

Reaktionsgleichung

Reaktionsgleichung von HRID 2300176
Cl[C:2]1(Cl)[C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4][C:3]1=[O:18].[Cl-].[NH4+]>CO.[Zn]>[O:18]=[C:3]1[CH2:2][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4]1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 9857764Tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

Produkt 1

HCID 11195798Tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylateAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

106.1 g zinc dust was added to a mixture of 62.5 g tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate and 500 ml saturated ammonium chloride in methanol. The mixture was stirred for 1 hr and 20 min at room temperature and filtered through Celite. The filtrate was evaporated, 1 N hydrochloric acid/ethyl acetate was added thereto, and the organic layer was recovered. The extract was washed with water, saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated, and the resulting residue was subjected to silica gel column chromatography to give 38.9 g of tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate.

Aufarbeitung

  1. filtrationfiltered through Celite
  2. customThe filtrate was evaporated
  3. addition1 N hydrochloric acid/ethyl acetate was added
  4. customthe organic layer was recovered
  5. washThe extract was washed with water, saturated sodium bicarbonate and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-38d760197e4b4f2c8c387a4995dfd709
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498159B1

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