Nitrogen → HCID 131735722, Verbindung

HRID 2201739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2201739
N#N.[CH3:3][C:4]([CH3:22])([O:6][C@H:7]1[C@@:15]2([CH3:16])[C@@H:10]([CH2:11][C:12]([OH:21])=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH2:14]2)[CH2:9][CH2:8]1)[CH3:5].[CH2:23]=[CH:24][C:25](=[O:31])[CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30]>C(Cl)Cl>[CH3:5][C:4]([CH3:22])([O:6][C@H:7]1[C@@:15]2([CH3:16])[C@@H:10]([CH2:11][C:12](=[O:21])[C:13]([CH2:23][CH2:24][C:25](=[O:31])[CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30])([C:17]([O:19][CH3:20])=[O:18])[CH2:14]2)[CH2:9][CH2:8]1)[CH3:3]

Komponenten

5

Edukt 3

HCID 947NitrogenHCID 118047521,7-Octadien-3-oneHCID 131735723HCID 131735723, Verbindung

Produkt 1

HCID 131735722HCID 131735722, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

Neutral alumina (15 g) was heated in a flask at 180° C. under high vacuum for 4 h. After cooling down to room temperature, the flask was filled with N2. Compound 31 (7.2 g, 25.5 mmol), 1,7-octadien-3-one (4.3 g, 30 mmol), and CH2Cl2 (30 mL) were added to the anhydrous alumina at room temperature. The mixture was stirred at room temperature for 16 h. The suspension was filtered through Celite® 545 which was washed with CH2Cl2 (100 mL×3). The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes) to afford compound 32 (9.4 g, 91%). The compound is a mixture of diastereomers at position C-5 in a 3 to 1 ratio. The major diastereomer had: 1H NMR (CDCl3) δ 5.72-5.60 (m, 1H), 4.95-4.86 (m, 2H), 3.64 (s, 3H), 3.35 (t, J=7.1 Hz, 1H), 1.05 (s, 9H), 0.75 (s, 3H); 13C NMR (CDCl3) δ 209.5, 208.0, 173.7, 137.8, 115.0, 79.9, 72.4, 56.2, 52.2, 46.9, 45.5, 42.4, 42.1, 41.7, 38.1, 32.9, 31.3, 30.5, 28.6, 28.4, 25.5, 22.6; IR νmax 1714, 1641, 1435 cm−1. Anal. Calcd for (C24H38O5): C, 70.90; H, 9.42. Found: C, 71.16; H, 9.70.

Aufarbeitung

  1. temperatureAfter cooling down to room temperature
  2. filtrationThe suspension was filtered through Celite® 545 which
  3. washwas washed with CH2Cl2 (100 mL×3)
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1d0793dc58c448d3b0be44769a0f3fc1
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365502B2

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