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Pyridine → N-(1,4-Dioxaspiro[4,5]dec-8-yl)-2,2,N-trimethylpropionamide

HRID 1748613
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1748613
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8](CN)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[C:13]([O:19]C(=O)C(C)(C)C)(=O)[C:14]([CH3:17])([CH3:16])[CH3:15].[N:26]1C=CC=C[CH:27]=1>CN(C)C1C=CN=CC=1>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([N:26]([CH3:27])[C:13](=[O:19])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 15234Pivalic anhydrideHCID 109539781-{1,4-Dioxaspiro[4.5]decan-8-yl}methanamine

Produkt 1

HCID 79111757N-(1,4-Dioxaspiro[4,5]dec-8-yl)-2,2,N-trimethylpropionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of (1,4-dioxaspiro[4,5]dec-8-yl)methylamine (11.0 g) in pyridine (64 ml) were added 4-dimethylaminopyridine (catalyst quantity) and pivalic acid anhydride (26.0 ml), and stirred at 90° C. for 2 hours. After completion of the reaction, the solvent was evaporated, ethyl acetate was added thereto, and sequentially washed with 1 N hydrochloric acid aqueous solution, 1 N aqueous solution of sodium hydroxide, and saturated brine. The organic layer was dried over sodium sulfate, then the solvent was evaporated, and the obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (12.9 g) as a pale brown oil. MS (ESI) m/z: 256 (M+H)+.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. additionethyl acetate was added
  4. washsequentially washed with 1 N hydrochloric acid aqueous solution, 1 N aqueous solution of sodium hydroxide, and saturated brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customthe solvent was evaporated
  7. customthe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f97e50e5072c4820af1c28a4db81b237
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09150555B2

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