Succinic anhydride → Salvinorin A

HRID 1509365Notes

Reaction equation

HRID 1509365 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 128563Salvinorin A

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-82dd4338f69d45bfb15f0f0965eaa3cd
Source dataset
uspto-grants-2015_12
Patent number
US09222949B2

Reaction notes

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