2-Azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid ethyl ester synthesis

Yield:3693-69-4 45%

Reaction Conditions:

with boron trifluoride diethyl etherate in benzene; for 1 h;Reflux;

Steps:

4

A solution of BF3-etherate (1.60 mL, 13.0 mmol) and methylene bisurethane (9.89 g, 52 mmol) in 70 mL of benzene was brought to reflux. A solution of 1 , 3-hexadiene in 10 mL of benzene was then added dropwise and the mixture was refluxed for 1 hr . After cooling, the mixture was washed with saturated NaHC03 and water, dried over MgS04, and concentrated in vacuo to yield an oily residue. This was distilled under vacuum to yield the product ( 16 , 45% yield) (Borne, R.F. et al, 1973))

References:

WO2013/28999,2013,A1 Location in patent:Page/Page column 76; 77