Potassium Carbonate → Cis-1-Methyl-3-[(9Z,12Z)-Octadeca-9,12-Dien-1-Yloxy]-4-(Octyloxy)Pyrrolidine

HRID 2176956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2176956
[CH2:1]([O:19][CH:20]1[CH:24]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:23][N:22]([C:34](OCC2C=CC=CC=2)=O)[CH2:21]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O-])([O-])=O.[K+].[K+].CC(OC)(C)C>C1COCC1>[CH3:34][N:22]1[CH2:23][C@H:24]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C@H:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:21]1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 21226445Aluminium lithium hydrideHCID 86694890Benzyl 3-[(9Z,12Z)-Octadeca-9,12-Dien-1-Yloxy]-4-(Octyloxy)Pyrrolidine-1-Carboxylate

Produkt 1

HCID 86694891Cis-1-Methyl-3-[(9Z,12Z)-Octadeca-9,12-Dien-1-Yloxy]-4-(Octyloxy)Pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a 100 mL RBF fitted with reflux condenser, compound 10 (4 g, 6.69 mmol) was dissolved in 26 mL THF for addition of the lithium aluminum hydride (13.38 ml, 13.38 mmol). Heated to reflux in a 85 C. oil bath. After 2 h, HPLC shows complete dissappearance of the SM. Cooled to RT and poured into 200 mL IM K2CO3 and 200 mL MTBE. Stirred for 30 min, separated layers and then extracted with 100 mL MTBE. Dried combined organics over Na2SO4, filtered through Celite and concentrated. Flash chromatography (10-30% IPA in DCM) provided compound 11 as a clear oil. 1H NMR (400 MHz, CDCl3) δ 5.39 (m, 4H), 3.93 (m, 2H), 3.50 (m, 4H), 3.04 (m, 2H), 2.79 (m, 2H), 2.48 (m, 2H), 2.39 (s, 3H), 2.08 (m, 4H), 1.62 (m, 4H), 1.40-1.25 (m, 26H), 0.91 (m, 6H).

Aufarbeitung

  1. customIn a 100 mL RBF fitted
  2. temperaturewith reflux condenser
  3. temperatureHeated
  4. temperatureto reflux in a 85 C
  5. customseparated layers
  6. extractionextracted with 100 mL MTBE
  7. customDried
  8. filtrationfiltered through Celite
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-be325cd766ec4b4095c34b278be9a385
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067882B2

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