Acetic Acid → HCID 57054788, Verbindung

HRID 1078719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1078719
C[O:2][C:3](=[O:21])[C@@H:4]1[CH2:8][C@@H:7]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:6][N:5]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[Cl-].[Li+].[BH4-].[Na+].[C:26](O)(=[O:28])C>O1CCCC1CO.O.C(OCC)(=O)C>[C:17]([O:16][C:14]([N:5]1[CH2:6][C@H:7]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:8][C@:4]1([CH2:26][OH:28])[C:3]([OH:2])=[O:21])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 147726821-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 57054788HCID 57054788, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 7360Tetrahydrofurfuryl alcoholLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (2S,4R)-N-tert-butoxycarbonyl-4-methanesulfonyloxyproline methyl ester (10.0 g, 30.9 mmol) in tetrahydrofuran--methanol (1:1, 100 ml) were successively added lithium chloride (3.93 g, 92.8 mmol) and sodium borohydride (3.51 g, 92.8 mmol). The reaction solution was stirred at room temperature for 11 h. Acetic acid (2 ml) was added to the reaction solution, and ethyl acetate and water were added thereto. The mixture was concentrated in vacuo. The residue was dissolved in water and ethyl acetate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to obtain a residue of (2S,4R)-N-tert-butoxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxyproline (9.41 g).

Aufarbeitung

  1. additionwere added
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionethyl acetate and extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9853c9091ad24a42995e6ad36451466c
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05550121

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