Benzyl chloroformate → (R)-benzyl 3-methyl-3-((R)-2-oxo-4-phenyloxazolidine-3-carbonyl)pyrrolidine-1-carboxylate

HRID 338826

Reaktionsgleichung

Reaktionsgleichung von HRID 338826
C([N:8]1[CH2:12][CH2:11][C@:10]([CH3:27])([C:13]([N:15]2[C@H:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][O:17][C:16]2=[O:26])=[O:14])[CH2:9]1)C1C=CC=CC=1.C([O-])(O)=O.[Na+].[CH2:33]([O:40][C:41](Cl)=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>ClCCCl.Cl>[CH3:27][C@@:10]1([C:13]([N:15]2[C@H:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][O:17][C:16]2=[O:26])=[O:14])[CH2:11][CH2:12][N:8]([C:41]([O:40][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:42])[CH2:9]1

Komponenten

6

Edukt 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 70983198(R)-3-((S)-1-benzyl-3-methylpyrrolidine-3-carbonyl)-4-phenyloxazolidin-2-one

Produkt 1

HCID 86707397(R)-benzyl 3-methyl-3-((R)-2-oxo-4-phenyloxazolidine-3-carbonyl)pyrrolidine-1-carboxylateAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittel2×HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

To a suspension of (R)-3-((S)-1-benzyl-3-methylpyrrolidine-3-carbonyl)-4-phenyloxazolidin-2-one (145.50 g, 399.25 mmol) and NaHCO3 (33.54 g, 399.25 mmol) in dry DCE (1000 mL) at ambient temperature was added dropwise a solution of benzylchloroformate (134.87 mL, 958.19 mmol) in DCE (100 mL) and the reaction was stirred at ambient temperature for 24 hours. The reaction was diluted with 1N HCl (500 mL) and the layers were separated. The organic layer was washed with 1M HCl (250 mL), dried (MgSO4), filtered and concentrated under reduced pressure to a thick yellow residue. The residue was purified by flash chromatography (5% ethyl acetate/DCM) to give (R)-benzyl 3-methyl-3-((R)-2-oxo-4-phenyloxazolidine-3-carbonyl)pyrrolidine-1-carboxylate (85.1 g, 208.35 mmol, 52.2% yield).

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic layer was washed with 1M HCl (250 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to a thick yellow residue
  6. customThe residue was purified by flash chromatography (5% ethyl acetate/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-b5e7317898804ea0a861439111aac533
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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