N-methyl-2-pyrrolidone → tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

HRID 234172

Reaktionsgleichung

Reaktionsgleichung von HRID 234172
Cl[CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([OH:14])=[O:13])[CH2:4]1.[CH3:15][C:16](Cl)([CH3:18])[CH3:17].CN1CCCC1=[O:26]>C([O-])(=O)C.C([N+](CCCC)(CCCC)CCCC)CCC>[OH:26][CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14][C:16]([CH3:18])([CH3:17])[CH3:15])=[O:13])[CH2:4]1

Komponenten

4

Edukt 2

HCID 13387N-methyl-2-pyrrolidoneHCID 86747487chloride (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid, 1,1-dimethylethyl ester

Produkt 1

HCID 9816650tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 82707Tetrabutylammonium AcetateKatalysator

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Solid tetra-n-butylammonium acetate prepared in step (e) (i) of Example 1 above (106.2 g, 0,352 mole) was added in one portion to a mechanically stirred solution of the chloride (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid, 1,1-dimethylethyl ester prepared in step (d) of Example 1 above (32.7 g, 0. 117 mole) in HPLC grade 1-methyl-2-pyrrolidinone (471 ml) under argon. The resulting solution was stirred at 85° C. (internal temperature). After 30 to 60 minutes the reaction mixture became homogeneous and brown in color. The progress of the reaction was followed by TLC and GC analysis. (TLC: Rf =0.54 for the title compound; Rf =0.63 for the chloride starting material (silica gel, Ethyl acetate: Hexane, 1:1, visualization by Ce(SO4)2 spray).) After 9 hours the reaction was completed.

Quellen und Nachweise

ORD-Eintrag
ord-99a94e6f467549aa866a2c98272f1fd7
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594153

Verknüpfte Notizen

Wird geladen…