Sodium Bicarbonate → HCID 46832153, compound

HRID 453724Notes

Reaction equation

HRID 453724 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+]>C1COCC1.O.CCOC(C)=O>[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

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 25242485HCID 25242485, compound

Product 1

HCID 46832153HCID 46832153, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

12-epi-Salvinorin A (52 mg, 0.12 mmol) was dissolved in THF (3 mL) and H2O (3 mL). To this solution was added NaHCO3 (202 mg, 2.4 mmol), and the reaction was stirred at rt for two hours. The mixture was then diluted with EtOAc, washed with brine, and dried over MgSO4. After evaporation of the solvent, flash chromatography (0% to 5% MeOH in hexanes) gave alcohol 35 as an off-white solid. (27 mg, 58% yield); Rf 0.16 (98:2, CH2Cl2/MeOH); 1H NMR (300 MHz, CDCl3) δ 7.43 (m, 1H), 7.41 (t, J=1.6, 1H), 6.41 (m, 1H), 5.30 (dd, J=6.1, 11.5, 1H), 4.21-3.97 (m, 1H), 3.72 (s, 3H), 2.73 (dd, J=3.1, 13.5, 1H), 2.53-2.41 (m, 3H), 2.34 (dd, J=11.6, 14.6, 1H), 2.18-1.93 (2H), 1.92-1.69 (m, 4H), 1.63 (m, 1H), 1.39 (s, 3H), 1.04 (s, 3H).

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. customAfter evaporation of the solvent, flash chromatography (0% to 5% MeOH in hexanes)

Sources & evidence

ORD record
ord-712a0ea98fde47ed952e4d2e74028b11
Source dataset
uspto-grants-2013_07
Patent number
US08492564B2

Reaction notes

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