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 1190069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1190069
C[O:2][C:3](=O)[CH2:4][C:5]1([CH2:15][N+:16]([O-])=O)[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1>CO.[Ni]>[O:12]1[C:8]2([CH2:13][CH2:14][C:5]3([CH2:4][C:3](=[O:2])[NH:16][CH2:15]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 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (8-nitromethyl-1,4-dioxa-spiro[4.5]dec-8-yl)-acetic acid methyl ester (5.34 g, 19.5 mmol) in 35 mL of methanol was purged with nitrogen. A portion of about 430 mg of Raney 2800 nickel was added. The reaction mixture was purged with hydrogen and a positive pressure of hydrogen was maintained overnight using a balloon. Then, the final mixture was purged with nitrogen and filtered through a pad of celite washing with methanol. The filtrate was concentrated to afford 1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-11-one (3.95 g, 96%) as a white solid.

Aufarbeitung

  1. customThe reaction mixture was purged with hydrogen
  2. temperaturea positive pressure of hydrogen was maintained overnight
  3. customThen, the final mixture was purged with nitrogen
  4. filtrationfiltered through a pad of celite
  5. washwashing with methanol
  6. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-d599d1b571154247b1a223093ecc781d
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674118B2

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