Triethylamine → Mesyl Salvinorin B

HRID 12316

Reaktionsgleichung

Reaktionsgleichung von HRID 12316
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:18][C@H:17]([OH:19])[C:16](=[O:20])[C@H:15]2[C@@:6]1([CH3:28])[CH2:7][CH2:8][C@H:9]1[C@:14]2([CH3:21])[CH2:13][C@@H:12]([C:22]2[CH:26]=[CH:25][O:24][CH:23]=2)[O:11][C:10]1=[O:27])=[O:4].[CH3:29][S:30](Cl)(=[O:32])=[O:31].CCN(CC)CC>C(Cl)Cl>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:18][C@H:17]([O:19][S:30]([CH3:29])(=[O:32])=[O:31])[C:16](=[O:20])[C@H:15]2[C@@:6]1([CH3:28])[CH2:7][CH2:8][C@@H:9]1[C@:14]2([CH3:21])[CH2:13][C@@H:12]([C:22]2[CH:26]=[CH:25][O:24][CH:23]=2)[O:11][C:10]1=[O:27])=[O:4]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11395172(2S,4aS,6aR,7R,9S,10aS,10bR)-9-(hydroxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

Produkt 1

HCID 11271318Mesyl Salvinorin BAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 8a (0.05 g, 0.13 mmol), methanesulfonyl chloride (1 mL) and NEt3 (2 mL) in CH2Cl2 (30 mL) was stirred at room temperature overnight and then the mixture was washed with saturated NaHCO3 (20 mL) and saturated NaCl (2×15 mL) and dried (Na2SO4). The solvent was removed under reduced pressure. The resulting crude solid was purified by column chromatography (eluent: ethyl acetate/n-hexanes) to afford 0.02 g (32%) of a white solid, mp 147-150° C.; 1H NMR (CDCl3): δ 1.14 (3H, s, H-19); 1.47 (3H, s, H-20); 1.50-1.70 (3H, m, H-7α,β and H-11β); 1.81 (1H, m, H-6α); 2.11 (1H, dd, J=2.9, 11.3 Hz, H-8); 2.16 (1H, s, H-10); 2.19 (1H, m, H-6β); 2.42 (1H, dd, J=13.2, 13.2 Hz, H-3α); 2.50 (1H, m, H-3β); 2.52 (1H, dd, J=4.8, 13.2 Hz, H-11α); 2.75 (1H, dd, J=3.6, 13.2 Hz, H-4); 3.25 (3H, s, CH3SO2); 3.74 (3H, s, CO2CH3); 5.07 (1H, dd, J=8.0, 12.2 Hz, H-2); 5.55 (1H, dd, J=5.1, 11.7 Hz, H-12); 6.41 (1H, dd, J=0.9, 1.8 Hz, H-14); 7.42 (1H, dd, J=1.8, 1.8 Hz, H-15); 7.45 (1H, br d).

Aufarbeitung

  1. washthe mixture was washed with saturated NaHCO3 (20 mL) and saturated NaCl (2×15 mL)
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was removed under reduced pressure
  4. customThe resulting crude solid was purified by column chromatography (eluent: ethyl acetate/n-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d9a5df717c8f4c4e9915b036f94d0c9a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728001B2

Verknüpfte Notizen

Wird geladen…