Sodium Hydroxide → HCID 20339672, compound

Participants

Reaction Steps

6.5 Parts of 2,2-diphenyl-3-(1-azabicyclo[2.2.2]-oct-2-yl)propionic acid hydrochloride is dissolved in 47 parts methanol. Then a solution of 0.7 part sodium hydroxide in 12 parts methanol is added, followed by 0.9 part 2,2-diphenyl-3-(1-azabicyclo[2.2.2]oct-2-yl)propionic acid and a solution of 2.7 parts methyl sulfate in 12 parts methanol. The resulting mixture is then refluxed for 20 minutes, cooled and stripped in vacuo. The gummy residue is partitioned between 90 parts by volume of a 2% sodium hydroxide solution and ethyl ether. The ether layer is separated, dried over anhydrous sodium sulfate and stripped in vacuo to afford as a gummy residue, methyl 2,2-diphenyl-3-(1-azabicyclo[2.2.2]oct-2-yl)propionate. The aqueous layer is adjusted to pH 7.9 with dilute hydrochloric acid, saturated with sodium chloride and extracted 6 times with portions of chloroform. The chloroform extracts are combined, dried over anhydrous sodium sulfate and stripped in vacuo to give 2,2-diphenyl- 3-(1-azabicyclo[2.2.2]oct-2-yl)propionic acid (starting material). This solid is refluxed with 2.0 parts methyl sulfate and 35 parts methanol for 18 minutes and then worked up as before to afford a second yield of the desired methyl 2,2-diphenyl-3-(1-azabicyclo[2.2.2]oct-2-yl)propionate.

Provenance & Evidence