1-Phenethylamine, (-)- → HCID 59492949, compound

HRID 1799035Notes

Reaction equation

HRID 1799035 reaction equation
[C:1]1([C@@H](N)C)C=CC=CC=1.[Cl:10][C:11]1[C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([OH:28])([C:24]([F:27])([F:26])[F:25])[C:15]=2[CH:14]=[C:13]([C:29]([OH:31])=[O:30])[CH:12]=1>C(OCC)(=O)C>[CH3:1][O:30][C:29]([C:13]1[CH:12]=[C:11]([Cl:10])[C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([OH:28])([C:24]([F:26])([F:27])[F:25])[C:15]=2[CH:14]=1)=[O:31]

Participants

4

Reactant 2

HCID 758181-Phenethylamine, (-)-2×HCID 59492938HCID 59492938, compound2×

Product 1

HCID 59492949HCID 59492949, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under an argon atmosphere, (S)-(−)-1-phenylethylamine (0.392 ml) and a seed crystal of a salt of an optically active form of 4-chloro-9-hydroxy-9-trifluoromethyl-9H-fluorene-2-carboxylic acid and (S)-(−)-1-phenylethylamine were added to a mixture of 4-chloro-9-hydroxy-9-trifluoromethyl-9H-fluorene-2-carboxylic acid (1.000 g) and ethyl acetate (5 ml), and the mixture was stirred at room temperature for 3 days. This suspension was filtered, and the obtained solid was washed with ethyl acetate (3 ml). The solid was dried under reduced pressure to give the title compound (0.466 g). The solid was analyzed under HPLC analysis condition 4 to find that an isomer with a long retention time was the main component.

Workup

  1. filtrationThis suspension was filtered
  2. washthe obtained solid was washed with ethyl acetate (3 ml)
  3. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-de87e1c77c864777b6fb4ecc1cc83b8a
Source dataset
uspto-grants-2013_01
Patent number
US08343994B2

Reaction notes

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