Methyl morpholine oxide → benzyl (2S)-2-isopropyl-3-oxopyrrolidine-1-carboxylate

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Reaktionsgleichung

[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C@H:3]1[CH:17]([CH3:19])[CH3:18].C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.C(#N)C>[CH:17]([C@H:3]1[C:2](=[O:1])[CH2:6][CH2:5][N:4]1[C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])([CH3:19])[CH3:18]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution (26 mL) of benzyl (2S)-3-hydroxy-2-isopropylpyrrolidine-1-carboxylate (3.22 g) in dehydrating acetonitrile were added molecular sieves 4A powder (2.31 g) and 4-methylmorpholine-N-oxide (2.86 g), and the mixture was cooled to 0° C. tetra-n-Propylammonium perruthenate (0.16 g) was added, and the mixture was stirred at 0° C. for 1 hr and at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in ethyl acetate. The insoluble material was filtered through Hyflo Super-Cel. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→4:1) to give the title compound as colorless oil (yield: 2.74 g).

Aufarbeitung

additionwas added
concentrationThe reaction mixture was concentrated under reduced pressure
filtrationThe insoluble material was filtered through Hyflo Super-Cel
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→4:1)

Quellen und Nachweise

ORD-Eintrag: ord-e71c75ba89ba4e39aa10e99bb7feae3e
Quelldatensatz: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08013008B2

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