Hydrochloric Acid → 2-Propanyl 4-[(3S,5aR,6R,7R,8aS)-7-(tetrahydro-2H-pyran-2-yloxy)-6-vinyloctahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate

HRID 573534

Reaktionsgleichung

Reaktionsgleichung von HRID 573534
[CH3:1][Si](C)(C)N[Si](C)(C)C.[Na].[CH:11]([C@@H:13]1[C@@H:22]2[C@@H:16]([O:17][CH2:18][C@@H:19]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[CH2:20][CH2:21]2)[CH2:15][C@H:14]1[O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1)=O.Cl>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[O:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH:33]1[O:32][C@@H:14]1[CH2:15][C@@H:16]2[O:17][CH2:18][C@@H:19]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[CH2:20][CH2:21][C@@H:22]2[C@H:13]1[CH:11]=[CH2:1]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 45051731Sodium hexamethyidisilazaneHCID 866653202-Propanyl 4-[(3S,5aR,6R,7R,8aS)-6-formyl-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate

Produkt 1

HCID 867043622-Propanyl 4-[(3S,5aR,6R,7R,8aS)-7-(tetrahydro-2H-pyran-2-yloxy)-6-vinyloctahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methyltriphenylphosphonium bromide (2.60 g) was suspended in THF (10 mL), and followed by cooling to 0° C. Sodium hexamethyldisilazane (7.0 mL, 1 mol/L THF solution) was added, followed by stirring at the same temperature for 30 minutes. A THF (1 mL) solution of the compound (1.0 g) produced in Example 13 was added dropwise, followed by stirring at the same temperature for 1 hour. An extract obtained by pouring the reaction solution to 1 N hydrochloric acid cooled to 0° C. and extracting with ethyl acetate was washed with water, an aqueous saturated sodium bicarbonate solution and a saturated saline; dried with anhydrous magnesium sulfate; and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain a titled compound (967 mg) having the following physical property values.

Aufarbeitung

  1. stirringby stirring at the same temperature for 1 hour
  2. customAn extract obtained
  3. temperaturecooled to 0° C.
  4. extractionextracting with ethyl acetate
  5. washwas washed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationand then concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bd540076a60543fd9d194c3f5b1d297e
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029574B2

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