Acetyl chloride → Ethyl 1-acetyl-8-oxa-1-azaspiro[4.5]decane-2-carboxylate

HRID 454453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454453
[NH:1]1[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][CH:2]1[C:11]([O:13][CH2:14][CH3:15])=[O:12].CCN(C(C)C)C(C)C.[C:25](Cl)(=[O:27])[CH3:26]>ClCCl>[C:25]([N:1]1[C:5]2([CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[CH2:4][CH2:3][CH:2]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:27])[CH3:26]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 58313084Ethyl 8-oxa-1-azaspiro[4.5]decane-2-carboxylate

Produkt 1

HCID 58313107Ethyl 1-acetyl-8-oxa-1-azaspiro[4.5]decane-2-carboxylateAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 8-oxa-1-azaspiro[4.5]decane-2-carboxylate (166) (135 mg, 0.63 mmol) in anhydrous dichloromethane (2 mL) was added Hunig's base (0.22 mL, 1.3 mmol) followed by acetyl chloride (0.05 mL, 0.76 mmol) and the reaction stirred at room temperature under nitrogen for 1.5 h. The reaction was diluted with dichloromethane and washed with 0.1 N HCl and the organic layer dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 60-100% hexanes/EtOAc to afford the title compound as a yellow oil (94 mg, 58% yield).

Aufarbeitung

  1. washwashed with 0.1 N HCl
  2. dry with materialthe organic layer dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 60-100% hexanes/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-11857d479fd9406d95fb70bca6b86908
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492554B2

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