3-Cyclohexene-1-carboxylic acid, 4-borono-, 1-ethyl ester synthesis

Yield:1443112-50-2 35 mg

Reaction Conditions:

with sodium periodate;ammonium acetate in water;acetone at 20;Cooling with ice;

Steps:

79.79a (Example 79a)[4- (ethoxycarbonyl) cyclohex-1-en-1-yl]boronic acid

4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) cyclohex-3-ene-1-carboxylic acid ethyl ester (200 mg)Acetone (6 mL),To a mixture of water (6 mL), under ice-cooling,Ammonium acetate (165 mg),And sodium periodate (458 mg), and the mixture was stirred overnight at room temperature.Ethyl acetate and water were added to the reaction solution, and the mixture was extracted four times. The organic layer was dried over magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (ethyl acetate / hexane)To give the title compound (35.0 mg) as a colorless oil.

References:

JP2016/141632,2016,A Location in patent:Paragraph 0542; 0544