Sodium Iodide → HCID 131730726, compound

HRID 453725Notes

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.[Na+].[I-].C(N(C(C)C)CC)(C)C.Cl[CH2:41][O:42][CH2:43][CH3:44]>CC(N(C)C)=O.CCOC(C)=O>[CH3:44][CH2:43][O:42][CH2:41][O:7][CH2:6][O:8][CH2:9][CH3:24].[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

Participants

Conditions

Temperature: 80 °C

Procedure

12-epi-Salvinorin B (15 mg, 0.038 mmol) was dissolved in DMA (500 μL) under argon. To this solution was added NaI (23 mg, 0.15 mmol), diisopropylethylamine (37 μL, 0.21 mmol), and chloromethylethyl ether (16 μL, 0.19 mmol). This solution was warmed to 80° C., and stirred for 18 hours. The mixture was then cooled to rt and diluted with EtOAc, washed with water and brine, and dried over MgSO4. After evaporation of the solvent, flash chromatography (0% to 70% EtOAc in hexanes) gave ethoxymethyl ether 37 as an off-white solid. (11.2 mg, 65% yield); Rf 0.28 (98:2, CH2Cl2/MeOH); 1H NMR (300 MHz, CDCl3) δ 7.43 (m, 1H), 7.40 (t, J=1.7 Hz, 1H), 6.41 (m, 1H), 5.29 (dd, J=6.0, 11.6, 1H), 4.76 (q, J=7.2, 2H), 4.16 (dd, J=7.4, 12.2, 1H), 3.72 (s, 3H), 3.69-3.51 (m, 2H), 2.72 (dd, J=3.3, 13.3, 1H), 2.46-2.27 (m, 4H), 2.20 (m, 1H), 2.05-1.68 (m, 4H), 1.57 (m, 1H), 1.38 (s, 3H), 1.18 (t, J=7.1, 2H), 1.06 (s, 3H).

Workup

temperatureThe mixture was then cooled to rt
washwashed with water and brine
dry with materialdried over MgSO4
customAfter evaporation of the solvent, flash chromatography (0% to 70% EtOAc in hexanes)

Sources & evidence

ORD record: ord-bea4a8a2255b4b1799a8875d94be84b8
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492564B2

Reaction notes

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