Hydrochloric Acid → 2-Azaspiro[4.5]decan-8-one

HRID 1477963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1477963
O1[C:5]2([CH2:14][CH2:13][C:8]3([CH2:12][CH2:11][NH:10][CH2:9]3)[CH2:7][CH2:6]2)[O:4]CC1.Cl>CO>[CH2:9]1[C:8]2([CH2:13][CH2:14][C:5](=[O:4])[CH2:6][CH2:7]2)[CH2:12][CH2:11][NH:10]1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 826579751,4-Dioxa-10-azadispiro[4.2.4.2]tetradecane

Produkt 1

HCID 686527332-Azaspiro[4.5]decan-8-oneAusbeute 128,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecane (10 g, 50.69 mmol) in MeOH (100 mL) was added HCl aqueous solution (2 M, 30 mL, 60 mmol). The reaction mixture was stirred at rt overnight and then concentrated in vacuo. The residue was dissolved in water (100 mL) and adjusted to pH=8 with a saturated Na2CO3 aqueous solution, then extracted with DCM (200 mL×3). The combined organic phases were washed with brine (200 mL), dried over anhydrous Na2SO4, then filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/7) to give the title compound as a yellow solid (10 g, 100%).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (100 mL)
  3. extractionextracted with DCM (200 mL×3)
  4. washThe combined organic phases were washed with brine (200 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/7)

Quellen und Nachweise

ORD-Eintrag
ord-6456711c345941cfb4feeec7389cbc3e
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403801B2

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