Water → HCID 54162700, Verbindung

HRID 620791

Reaktionsgleichung

Reaktionsgleichung von HRID 620791
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][OH:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].O>O1CCCC1.CCCCCC.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][O:22][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11078078tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 178418339Butyllithium

Produkt 1

HCID 54162700HCID 54162700, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (2S,4R)-1-t-butoxycarbonyl-4-t-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine (1.00 g) in tetrahydrofuran (20 ml) was dropwise added a 1.6 M solution of butyllithium in hexane (2 ml) at -40°~-30° C. in a nitrogen stream and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was added ethyl bromoacetate (0.40 ml) at -40°~-30° C. and the reaction mixture was stirred at -40°~-30° C. for 30 minutes and then at ambient temperature for 3 hours. The mixture was poured into a mixture of water (50 ml) and ethyl acetate (50 ml). The organic layer was washed with brine (50 ml), dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (20 g) and eluted with chloroform to give (2S,4R)-1-t-butoxycarbonyl-4-t-butyldimethylsilyloxy-2-(ethoxycarbonylmethyloxymethyl)pyrrolidine (0.88 g).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at -40°~-30° C. for 30 minutes
  2. waitat ambient temperature for 3 hours
  3. washThe organic layer was washed with brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a syrup
  7. washeluted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-a35f83cd45634c3b95b15101fef6f8ba
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04822787

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