Sodium Hydroxide → HCID 20339672, compound

HRID 597229Notes

Reaction equation

HRID 597229 reaction equation
Cl.[C:2]1([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([CH2:12][CH:13]2[CH2:18][CH:17]3[CH2:19][CH2:20][N:14]2[CH2:15][CH2:16]3)[C:9]([OH:11])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:29]1(C(C2C=CC=CC=2)(CC2CC3CCN2CC3)C(O)=O)C=CC=CC=1.S([O-])(OC)(=O)=O>CO>[C:21]1([C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([CH2:12][CH:13]2[CH2:18][CH:17]3[CH2:19][CH2:20][N:14]2[CH2:15][CH2:16]3)[C:9]([O:11][CH3:29])=[O:10])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 4694097Methyl sulfate(1-)HCID 20339683HCID 20339683, compoundHCID 68123077HCID 68123077, compound

Product 1

HCID 20339672HCID 20339672, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

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.

Workup

  1. temperatureThe resulting mixture is then refluxed for 20 minutes
  2. temperaturecooled
  3. customThe gummy residue is partitioned between 90 parts by volume of a 2% sodium hydroxide solution and ethyl ether
  4. customThe ether layer is separated
  5. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-2feef62eed83495684bfb14736f48aca
Source dataset
uspto-grants-1977_03
Patent number
US04013667

Reaction notes

Loading…