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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence