Hydrochloric Acid → tert-Butyl (R)-6-Cyano-5-hydroxy-3-oxohexanoate

HRID 466294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 466294
[C:1]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])(=[O:3])[CH3:2].[C:9]([CH2:11][C@@H:12]([OH:21])[CH2:13][C:14](OCCCC)=[O:15])#[N:10].C([N-]C(C)C)(C)C.[Li+].Cl>O1CCCC1.C(OCC)(=O)C>[C:9]([CH2:11][C@@H:12]([OH:21])[CH2:13][C:14](=[O:15])[CH2:2][C:1]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3])#[N:10]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 10908tert-Butyl acetateHCID 2724682Lithium diisopropylamideHCID 54237719HCID 54237719, Verbindung

Produkt 1

HCID 9794547tert-Butyl (R)-6-Cyano-5-hydroxy-3-oxohexanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred -50° C. solution of tertiary-butyl acetate (60 mL, 0.44 mol), (R)-4-cyano-3-hydroxybutyric acid, n-butyl ester (20 g, 0.11 mol) and 150 mL tetrahydrofuran is added lithium diisopropylamide (300 mL of 1.5 M) in tetrahydrofuran over 15 minutes and the mixture is stirred at -45° C. to -50° C. for 90 minutes. To this solution is added 700 mL of 5% aqueous hydrochloric acid solution along with 300 mL of ethyl acetate. The aqueous layer is separated and the remaining top layer washed with aqueous sodium chloride solution. The organic layer is then concentrated in vacuo to afford crude (5R)-1,1-dimethylethyl 6-cyano-5-hydroxy-3-oxo-hexanoate which is not isolated, and is carried on to (4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl -1,3-dioxane-4-acetate as described in Example 2. TLC: Rf =0.15 (1:1 ethyl acetate: hexanes) on a Kieselgel 60 F254 0.254 mm silica thin layer plate.

Aufarbeitung

  1. customThe aqueous layer is separated
  2. washthe remaining top layer washed with aqueous sodium chloride solution
  3. concentrationThe organic layer is then concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f4b466fd58d1431cb4861a79b6b502d0
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155251

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