Trifluoroacetic acid → HCID 19775316, compound

HRID 1613187Notes

Reaction equation

HRID 1613187 reaction equation
[CH:1]([OH:14])([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.[NH2:15][C:16]1([CH2:21]O)[CH2:20][CH2:19][CH2:18][CH2:17]1.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl.O1CCOCC1>[NH2:15][C:16]1([CH2:21][O:14][CH:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7037BenzhydrolHCID 14798Sodium HydroxideHCID 663071-Aminocyclopentanemethanol

Product 1

HCID 19775316HCID 19775316, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Benzhydrol (1.6 g) was added in one portion to a solution of 1-aminocyclopentane-1-methanol (1.0 g) and trifluoroacetic acid (3.5 ml) in methylene chloride (10 ml) and the mixture was stirred at room temperature for 3 hours and then treated with dioxane (10 ml) and 4M aqueous sodium hydroxide solution. The mixture was stirred at room temperature for 30 minutes and evaporated. The residue was partitioned between water and ether and the organic layer was extracted into 2M hydrochloric acid. The acidic extract was washed with ether/hexane (1:1), basified with solid sodium carbonate and extracted into ether. The organic extracts were dried over magnesium sulphate and evaporated to give the title compound as a pale yellow oil which was characterised as containing 0.25 molar equivalents of water (710 mg, 30%).

Workup

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. customevaporated
  3. customThe residue was partitioned between water and ether
  4. extractionthe organic layer was extracted into 2M hydrochloric acid
  5. extractionThe acidic extract
  6. washwas washed with ether/hexane (1:1)
  7. extractionextracted into ether
  8. dry with materialThe organic extracts were dried over magnesium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-7635379595e343118dd8108b8e3d3649
Source dataset
uspto-grants-1993_03
Patent number
US05192765

Reaction notes

Loading…