Hydrochloric Acid → HCID 69083351, Verbindung

HRID 1525848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1525848
[CH:1]1([N:4]2[CH2:9][C:8]3([CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]3)[O:7][CH2:6][C:5]2=[O:22])[CH2:3][CH2:2]1.[ClH:23]>C(O)C.O1CCOCC1>[ClH:23].[CH:1]1([N:4]2[CH2:9][C:8]3([CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[O:7][CH2:6][C:5]2=[O:22])[CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 690854321,1-Dimethylethyl 4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Produkt 1

HCID 69083351HCID 69083351, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1,1-Dimethylethyl 4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate was dissolved in ethanol (300 mL) and cooled over an ice bath. A 4M solution of hydrogen chloride in dioxane (300 mL) was added, such that the temperature remained low. The ice bath was removed and the mixture was stirred at ambient temperature overnight. The solid was collected, washed with a little ethanol and diethyl ether to give the title product (47.1 g, 58%). The mother liquors were treated with diethyl ether (1.2 L), stirred for 30 min, and the solid was collected and dried to give a total combined yield of 78% of the title product (63.69 g) over the three steps. MS(ES)+ m/e 211.0[M+H+]; 1H NMR (400 MHz, DMSO-d6) δ 9.17-8.64 (m, 2 H), 4.04 (s, 2 H), 3.14 (d, J=13.1 Hz, 2 H), 3.01-2.85 (m, 2 H), 2.83-2.71 (m, 1 H), 1.96-1.83 (m, 2 H), 1.83-1.68 (m, 2 H), 0.76-0.67 (m, 2 H), 0.64-0.55 (m, 2 H).

Aufarbeitung

  1. temperaturecooled over an ice bath
  2. customThe ice bath was removed
  3. customThe solid was collected
  4. washwashed with a little ethanol and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-861792737eba48ada612069cc5f96277
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09084794B2

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