Acetic Acid → HCID 70092189, compound

HRID 2255415Notes

Reaction equation

HRID 2255415 reaction equation
[CH2:1]([C:3]1[CH:8]2[CH2:9][CH:10]([C:11]([O:13]CC)=[O:12])[CH:5]([N:6]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:7]2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:4]=1)[CH3:2].C(O)(=O)C.[BrH:34]>>[BrH:34].[C:24]1([CH2:23][N:6]2[CH:7]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:8]3[C:3](=[CH:1][CH3:2])[CH2:4][CH:5]2[CH:10]([C:11]([OH:13])=[O:12])[CH2:9]3)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 12880745HCID 12880745, compound

Product 1

HCID 70092189HCID 70092189, compound

Procedure

A mixture of ethyl 8-ethyl-2,3-di(phenylmethyl)-2-azabicyclo[2.2.2]oct-7-ene-6-carboxylate (132 g, 0.31 mol) in 48% HBr (1300 mL) was refluxed for 30 minutes, then acetic acid (650 mL) was added and the mixture was refluxed for an additional 24 hours. A precipitate formed which was collected by filtration and washed with acetic acid/ether to afford 20.8 g of 2.3-di(phenylmethyl)-8-ethylidene-2-azabicyclo[2.2.2]octane-6-carboxylic acid hydrobromide, m.p. 251°-253° C. (dec.). Additional crops of the product were obtained by cooling the filtrate in an ice-bath and collecting the crystals that formed by filtration. A total of 69.8 g (50%) of the product was obtained in this manner.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. temperaturethe mixture was refluxed for an additional 24 hours
  3. customA precipitate formed which
  4. filtrationwas collected by filtration
  5. washwashed with acetic acid/ether

Sources & evidence

ORD record
ord-68a1ceb4edb5434199e6953764bdafd6
Source dataset
uspto-grants-1993_08
Patent number
US05240935

Reaction notes

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