Succinic anhydride → Salvinorin A

HRID 1509365

Reaktionsgleichung

Reaktionsgleichung von HRID 1509365
[CH3:1][C@:2]12[C@H:17]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][C@H:15]([OH:22])[C:13](=[O:14])[C@@H:12]1[C@:11]1([CH3:23])[C@H:5]([C:6]([O:8][C@H:9]([C:24]3[CH:25]=[CH:26][O:27][CH:28]=3)[CH2:10]1)=[O:7])[CH2:4][CH2:3]2.C1(=O)O[C:32](=[O:33])[CH2:31]C1.C1CCN2C(=NCCC2)CC1>ClCCl>[CH3:31][C:32]([O:22][C@@H:15]1[C:13](=[O:14])[C@H:12]2[C@@:2]([CH3:1])([CH2:3][CH2:4][C@@H:5]3[C@:11]2([CH3:23])[CH2:10][C@@H:9]([C:24]2[CH:25]=[CH:26][O:27][CH:28]=2)[O:8][C:6]3=[O:7])[C@H:17]([C:18]([O:20][CH3:21])=[O:19])[CH2:16]1)=[O:33]

Komponenten

5

Edukt 3

HCID 7922Succinic anhydrideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11440685Salvinorin B

Produkt 1

HCID 128563Salvinorin A

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To Salvinorin B (190 mg, 0.487 mmol) and succinic anhydride (112 mg, 2.5 eq) suspended in dichloromethane (5 ml) at 0° C. was added DBU (218 pl, 3 eq) dropwise. The mixture was stirred at 0° C. for 15 mins, washed with 3% citric acid (5 ml), saturated NaHCO3 solution (5 ml) and brine (5 ml). The mixture was dried over sodium sulfate, filtered and evaporated to dryness. The crude residue was purified by column chromatography (silica gel: CH2Cl2 to 5% MeOH in CH2Cl2) to give salvinorin hemisuccinate (130 mg, 54%).

Aufarbeitung

  1. washwashed with 3% citric acid (5 ml), saturated NaHCO3 solution (5 ml) and brine (5 ml)
  2. dry with materialThe mixture was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude residue was purified by column chromatography (silica gel: CH2Cl2 to 5% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-82dd4338f69d45bfb15f0f0965eaa3cd
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09222949B2

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