Hydrochloric Acid → 2,9-Diazaspiro(5.5)undecan-1-one hydrochloride

HRID 41538

Reaktionsgleichung

Reaktionsgleichung von HRID 41538
[O:1]=[C:2]1[C:7]2([CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][NH:3]1.[ClH:20]>C(Cl)Cl.O1CCOCC1>[ClH:20].[C:2]1(=[O:1])[C:7]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][NH:3]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 49760149tert-Butyl 1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylate

Produkt 1

HCID 450742882,9-Diazaspiro(5.5)undecan-1-one hydrochlorideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To the stirred solution of tert-butyl 1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylate (3.0 g, 11.19 mmol) in DCM (60 mL) was added 4N HCl in dioxane (20 mL) and the mixture was stirred at rt for 18 h. The solvent was removed under reduced pressure and triturated with diethyl ether (2×5 mL) to yield the title compound as a solid (2.2 g, 96%). Note: The product is moisture sensitive. [1H-NMR (DMSO-d6, 300 MHz): δ 9.25-8.68 (m, 2H), 7.43 (s, 1H), 7.20-6.25 (m, 2H), 3.61-2.90 (m, 5H), 2.12-1.95 (m, 2H), 1.76-1.49 (m, 5H); LCMS RtA=0.326, [M+H]+=169.0].

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customtriturated with diethyl ether (2×5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-67defb743249464596a605a19e4e499a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530648B2

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