Water → Salvinorin B

HRID 1509364

Reaction equation

HRID 1509364 reaction equation
CC([O:4][C@@H:5]1[C:19](=[O:20])[C@H:18]2[C@@:8]([CH3:27])([CH2:9][CH2:10][C@@H:11]3[C@:17]2([CH3:21])[CH2:16][C@@H:15]([C:22]2[CH:23]=[CH:24][O:25][CH:26]=2)[O:14][C:12]3=[O:13])[C@H:7]([C:28]([O:30][CH3:31])=[O:29])[CH2:6]1)=O.C(=O)([O-])[O-].[Na+].[Na+].O>CO>[CH3:27][C@:8]12[C@H:7]([C:28]([O:30][CH3:31])=[O:29])[CH2:6][C@H:5]([OH:4])[C:19](=[O:20])[C@@H:18]1[C@:17]1([CH3:21])[C@H:11]([C:12]([O:14][C@H:15]([C:22]3[CH:23]=[CH:24][O:25][CH:26]=3)[CH2:16]1)=[O:13])[CH2:10][CH2:9]2

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 128563Salvinorin A

Product 1

HCID 11440685Salvinorin BYield 42.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Salvinorin A (500 mg, 1.15 mM) in methanol (10 ml) was added solid sodium carbonate (490 mg, 4.6 mM) and the mixture stirred at room temperature overnight. Water (20 ml) was added to mixture and the mixture stirred for 30 mins. The solution was filtered and the filter-cake washed with ice-cold water (20 ml) and ice-cold methanol (20 ml) and dried in a dessicator to give Salvinorin B (191 mg, 42%).

Workup

  1. stirringthe mixture stirred for 30 mins
  2. filtrationThe solution was filtered
  3. washthe filter-cake washed with ice-cold water (20 ml) and ice-cold methanol (20 ml)
  4. customdried in a dessicator

Sources & evidence

ORD record
ord-fde16edeb1b248fdb5fe3b8ab8ff05a5
Source dataset
uspto-grants-2015_12
Patent number
US09222949B2

Linked notes

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