Tetrabutylammonium Fluoride → HCID 59614360, Verbindung

HRID 409471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 409471
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][CH3:14])[CH2:11][C@H:10]([O:15][Si](C(C)(C)C)(C)C)[C@@H:9]1[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][CH3:14])[CH2:11][C@H:10]([OH:15])[C@@H:9]1[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 59614342HCID 59614342, Verbindung

Produkt 1

HCID 59614360HCID 59614360, VerbindungAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of (2S,3S,5R)-2-benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.243 mmol; 102 mg) in THF is added 1.0 M THF solution (0.36 mL) of tetra-n-butylammonium fluoride under nitrogen at room temperature. After 3 hours, The reaction mixture is quenched with saturated aqueous ammonium chloride solution, extracted three times with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4, filtered, concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc) to give (2S,3S,5R)-2-benzyl-5-ethyl-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (74.4 mg, 99%); ESI-MS m/z: 250 [M+−tBu+2], Retention time 2.34 min (condition A).

Aufarbeitung

  1. customThe reaction mixture is quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-c363b3fc180f41ceabbb3bd75639f8f2
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759365B2

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