3-oxohexanoic acid

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 g of resin-bound 2-oxopentanecarboxylic acid (1) are swollen in 200 ml of acetic acid and treated with 20 g of malonic acid (2). 10 g of anhydrous ammonium acetate are added and the mixture is heated to 50° C. After stirring carefully for 3 h, the resin is freed from the solution, washed thoroughly with DMF and methylene chloride and dried. 53 g of (3) are obtained. Removal of a sample using anhydrous TFA yields the free Meldrum's. acid derivative (3, Li-P=H) (HPLC, MS). washed thoroughly with DMF and methylene chloride dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In accordance with the procedure of Example 9, ethyl ester of 3-oxohexanoic acid as a substrate in place of ethyl ester of 2-methyl-3-oxobutyric acid was subjected to reduction by baker's yeast to obtain ethyl ester of (3R)-3-hydroxyhexanoic acid. This compound was subjected to methylation according to the process of the literature [G. Frater et al., Tetrahedron, 40, 1269 (1984)] as in Reference Example 3, to obtain ethyl ester of (2R, 3R)-3-hydroxy-2-methylhexanoic acid. This compound was converted to a methyl ether compound and then subjected to hydrolysis in accordance with the procedure of Example 11 to obtain the title compound.