Acetic Acid → (2s)-Benzhydryl-3-quinuclidinone l-tartaric acid salt

HRID 982872

Reaction equation

HRID 982872 reaction equation
[CH:1]([CH:14]1[C:19](=[O:20])[CH:18]2[CH2:21][CH2:22][N:15]1[CH2:16][CH2:17]2)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[C:27]([OH:36])(=[O:35])[C@@H:28]([C@H:30]([C:32]([OH:34])=[O:33])[OH:31])[OH:29]>C(O)C>[C:27]([OH:36])(=[O:35])[C@@H:28]([C@H:30]([C:32]([OH:34])=[O:33])[OH:31])[OH:29].[CH:1]([C@H:14]1[C:19](=[O:20])[CH:18]2[CH2:17][CH2:16][N:15]1[CH2:22][CH2:21]2)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4251102-Benzhydryl-3-quinuclidinoneHCID 444305L-Tartaric acid

Product 1

HCID 131724767(2s)-Benzhydryl-3-quinuclidinone l-tartaric acid salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Racemic 2-benzhydryl-3-quinuclidinone (52.45 g, 180 mmol) was dissolved in denatured ethanol (525 ml) with acetic acid (10.4 ml, 180 mmol) and L-tartaric acid (27 g, 180 mmol) was added. The mixture was heated to reflux for 12 hours and then allowed to cool to room temperature and held for one hour. The solids were collected and dried under vacuum at 40° C. for 12 hours. The yield of the desired salt was 69.9 g, 88% of theory.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 12 hours
  4. customThe solids were collected
  5. customdried under vacuum at 40° C. for 12 hours

Sources & evidence

ORD record
ord-395763701c28443a87cf1c2ec3dbf351
Source dataset
uspto-grants-2005_03
Patent number
US06861526B2

Linked notes

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