Tetrabutylammonium Fluoride → (2S,4R)-methyl 4-methoxy-4-(3'-vinylbiphenyl-3-yl)pyrrolidine-2-carboxylate

HRID 1043432Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1043432
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][O:20][C@:21]1([C:39]2[CH:40]=[C:41]([C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([CH:51]=[CH2:52])[CH:46]=3)[CH:42]=[CH:43][CH:44]=2)[CH2:25][N:24](C(OCC[Si](C)(C)C)=O)[C@H:23]([C:35]([O:37][CH3:38])=[O:36])[CH2:22]1>C1COCC1.CCOC(C)=O>[CH3:19][O:20][C@:21]1([C:39]2[CH:40]=[C:41]([C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([CH:51]=[CH2:52])[CH:46]=3)[CH:42]=[CH:43][CH:44]=2)[CH2:25][NH:24][C@H:23]([C:35]([O:37][CH3:38])=[O:36])[CH2:22]1

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 59266553(2S,4R)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-methoxy-4-(3'-vinylbiphenyl-3-yl)pyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 59266492(2S,4R)-methyl 4-methoxy-4-(3'-vinylbiphenyl-3-yl)pyrrolidine-2-carboxylateAusbeute 108,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

TBAF (1.0M in THF, 19 mL, 19 mmol) was added to a solution of (2S,4R)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-methoxy-4-(3′-vinylbiphenyl-3-yl)pyrrolidine-1,2-dicarboxylate (2.3 g, 4.78 mmol) in THF (30 mL) and stirred at r.t. overnight. The reaction was diluted with EtOAc and washed with water and then brine. The organic layer was collected, dried over MgSO4, filtered and evaporated to give (2S,4R)-methyl 4-methoxy-4-(3′-vinylbiphenyl-3-yl)pyrrolidine-2-carboxylate (1.75 g, 5.19 mmol, 100% yield) as a yellow oil. LCMS: rt=1.42 min. [M-OMe]+=306; Phenomenex-Luna C-18 (5μ) (3.0×50 mm); Solvent A=10% acetonitrile—90% water—0.1% TFA, Solvent B=90% acetonitrile—10% water—0.1% TFA; gradient 0% to 100% solvent B over 2 min. and then hold for 1 min.; 4 mL/min; inj. vol.=5 uL; wavelength=220.

Aufarbeitung

  1. washwashed with water
  2. customThe organic layer was collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f6bf45b2f71e41e0b9cb92c39907165d
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563505B2

Notizen zur Reaktion

Wird geladen…