Methyl 2-(8-(nitromethyl)-1,4-dioxaspiro[4.5]decan-8-yl)acetate → 1,4-Dioxa-10-azadispiro[4.2.4^{8}.2^{5}]tetradecan-11-one

HRID 1505691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505691
[N+:1]([CH2:4][C:5]1([CH2:15][C:16]([O:18]C)=O)[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1)([O-])=O>CO.[Pd]>[O:12]1[C:8]2([CH2:13][CH2:14][C:5]3([CH2:15][C:16](=[O:18])[NH:1][CH2:4]3)[CH2:6][CH2:7]2)[O:9][CH2:10][CH2:11]1

Komponenten

4

Edukt 1

HCID 57795518Methyl 2-(8-(nitromethyl)-1,4-dioxaspiro[4.5]decan-8-yl)acetate

Produkt 1

HCID 577954141,4-Dioxa-10-azadispiro[4.2.4^{8}.2^{5}]tetradecan-11-oneAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a slurry of Methyl [8-(nitromethyl)-1,4-dioxaspiro[4.5]dec-8-yl]acetate (1 g, 4.7 mmol) in Methanol (20 mL) was added Pd/C (1 g, 10%) under N2 atmosphere. The reaction mixture was stirred at room temperature under 5 kg/cm2 H2 pressure for 12 h. After completion, the reaction mixture was filtered through celite pad, washed with methanol and the filtrate was concentrated under reduced pressure to afford the title compound as a white solid (0.7 g, 70%). 1H NMR (400 MHz, DMSO-d6) δ 7.46 (s, 1H), 3.83 (s, 4H), 3.00 (s, 2H), 2.00 (s, 2H), 1.56-1.51 (m, 8H).

Aufarbeitung

  1. filtrationAfter completion, the reaction mixture was filtered through celite pad
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-de3228e0bb804093b6b745d511dbb4ce
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216991B2

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