Tetrahydrofuran → 5-Methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-6-morpholinocarbonyloxy-1-oxaspiro[2,5]octane

HRID 964354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 964354
[OH:1][CH:2]1[CH2:9][CH2:8][C:5]2([O:7][CH2:6]2)[CH:4]([C:10]2([CH3:18])[CH:12]([CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[O:11]2)[CH:3]1[O:19][CH3:20].O1CCCC1.[H-].[Na+].[O:28]1[CH2:33][CH2:32][N:31]([C:34](Cl)=[O:35])[CH2:30][CH2:29]1>C(OCC)C>[CH3:20][O:19][CH:3]1[CH:2]([O:1][C:34]([N:31]2[CH2:32][CH2:33][O:28][CH2:29][CH2:30]2)=[O:35])[CH2:9][CH2:8][C:5]2([O:7][CH2:6]2)[CH:4]1[C:10]1([CH3:18])[CH:12]([CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[O:11]1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 848104-Morpholinecarbonyl chlorideHCID 2190894-(1,5-Dimethyl-1,2-epoxy-4-hexenyl)-5-methoxy-1-oxaspiro(2.5)octan-6-ol

Produkt 1

HCID 149888575-Methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-6-morpholinocarbonyloxy-1-oxaspiro[2,5]octaneAusbeute 53,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 6-hydroxy-5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2,5]octane (14.1 mg) in freshly distilled tetrahydrofuran (0.5 ml) was added sodium hydride (2.0 mg, 60% oil dispersion) in one portion at 5° C. The mixture was stirred for half an hour at the same temperature and then morpholinocarbonyl chloride (6.8 mg) was added thereto. The reaction mixture was stirred for 2 hours at ambient temperature and diluted with diethyl ether (2 ml). The organic layer was washed with water, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (elution by diethyl ether/n-hexane=2/1) to yield 5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)-oxiranyl ]-6-(morpholinocarbonyloxy)-1-oxaspiro[2,5]octane (9.7 mg) as an oil.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 2 hours at ambient temperature
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (elution by diethyl ether/n-hexane=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-6ed755e09e394e389ae79f348528044c
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05767293

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