Tetrabutylammonium Fluoride → HCID 86676600, Verbindung

HRID 85637

Reaktionsgleichung

Reaktionsgleichung von HRID 85637
[Si]([O:8][CH2:9][CH2:10][NH:11][C@:12]12[CH2:47][CH2:46][C@@H:45]([C:48]([CH3:50])=[CH2:49])[C@@H:13]1[C@@H:14]1[C@@:27]([CH3:30])([CH2:28][CH2:29]2)[C@@:26]2([CH3:31])[C@@H:17]([C@:18]3([CH3:44])[C@@H:23]([CH2:24][CH2:25]2)[C:22]([CH3:33])([CH3:32])[C:21]([C:34]2[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=2)=[CH:20][CH2:19]3)[CH2:16][CH2:15]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[OH:8][CH2:9][CH2:10][NH:11][C@:12]12[CH2:47][CH2:46][C@@H:45]([C:48]([CH3:50])=[CH2:49])[C@@H:13]1[C@@H:14]1[C@@:27]([CH3:30])([CH2:28][CH2:29]2)[C@@:26]2([CH3:31])[C@@H:17]([C@:18]3([CH3:44])[C@@H:23]([CH2:24][CH2:25]2)[C:22]([CH3:33])([CH3:32])[C:21]([C:34]2[CH:35]=[CH:36][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:42][CH:43]=2)=[CH:20][CH2:19]3)[CH2:16][CH2:15]1

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 86676599methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(tert-butyldimethylsilyloxy)ethylamino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

Produkt 1

HCID 86676600HCID 86676600, VerbindungAusbeute 52,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(tert-butyldimethylsilyloxy)ethylamino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (0.211 g, 0.301 mmol) in THF (2 mL) was added TBAF (1M in THF) (0.601 mL, 0.601 mmol). The mixture was stirred at rt for 2.75 h then was diluted with water (10 mL) and was extracted with dichloromethane (3×10 mL). The combined organic layers were dried with Na2SO4, the drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was adsorbed to silica gel and was purified by flash chromatography using a 0-25% EtOAc in hexanes gradient. The title compound (93.4 mg, 0.159 mmol, 52.9% yield), was isolated as a colorless film. LCMS: m/e 588.6 (M+H)+, 1.98 min (method 2). 1H NMR (500 MHz, CHLOROFORM-d) d ppm 7.91 (d, J=8.24 Hz, 2H), 7.18 (d, J=8.24 Hz, 2H), 5.27 (d, J=4.58 Hz, 1H), 4.70 (d, J=1.83 Hz, 1H), 4.59 (s, 1H), 3.89 (s, 3H), 3.54-3.64 (m, 2H), 2.52-2.69 (m, 3H), 2.09 (dd, J=17.09, 6.41 Hz, 1H), 1.68 (s, 3H), 1.07 (s, 3H), 0.98 (s, 3H), 0.97 (s, 3H), 0.93-2.05 (m, 21H), 0.91 (s, 3H), 0.91 (s, 3H).

Aufarbeitung

  1. extractionwas extracted with dichloromethane (3×10 mL)
  2. dry with materialThe combined organic layers were dried with Na2SO4
  3. customthe drying agent was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d888745e473448e3b1b97427232b69e6
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846647B2

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