Diethyl Ether → Tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

HRID 2300175

Reaktionsgleichung

Reaktionsgleichung von HRID 2300175
[CH2:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(OCC)C.[Cl:20][C:21](Cl)([Cl:25])[C:22](Cl)=[O:23].C(=O)(O)[O-].[Na+]>C(COC)OC.[Cu].[Zn]>[Cl:20][C:21]1([Cl:25])[C:2]2([CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)[CH2:1][C:22]1=[O:23]

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 6420Trichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 27568081-Boc-4-Methylenepiperidine

Produkt 1

HCID 9857764Tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylateAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10290809Zinc copper coupleKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

49.3 g of tert-butyl 4-methylene-1-piperidine carboxylate was added to a mixture of 157.2 g zinc-copper alloy and 500 ml diethyl ether, and 900 ml solution of 181.8 g trichloroacetyl chloride in dimethoxyethane was added dropwise thereinto over 5.5 hours. After stirred for 30 min, the reaction solution was cooled and saturated aqueous sodium bicarbonate was added thereto at 0° C. or less. The mixture was filtered through Celite and evaporated. The resulting residue was extracted with ethyl acetate. The extract was washed with 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 62.5 g of tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate.

Aufarbeitung

  1. temperaturethe reaction solution was cooled
  2. customat 0° C. or less
  3. filtrationThe mixture was filtered through Celite
  4. customevaporated
  5. extractionThe resulting residue was extracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-73ed4dc326104f7ea5c9ada7ea8b7d5c
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498159B1

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