1-Phenethylamine, (+)- → HCID 57951154, compound

HRID 1919794Notes

Reaction equation

HRID 1919794 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:23])([F:22])[F:21])[CH:14]=3)[CH2:11][C:10](=O)[C:9]2=[O:25])=[CH:4][CH:3]=1.[CH3:26][C@@H:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:23])([F:21])[F:22])[CH:14]=3)[CH:11]=[C:10]([NH:34][C@@H:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH3:26])[C:9]2=[O:25])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 67500774HCID 67500774, compound

Product 1

HCID 57951154HCID 57951154, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve (±)-1-(4-bromo-phenyl)-5-(3-trifluoromethoxy-phenyl)-pyrrolidine-2,3-dione (14.6 g, 35.2 mmol) in dichloromethane (35 mL). Add (R)-(+)-α-methylbenzylamine (6.8 mL, 52.8 mmol) and stir overnight at ambient temperature. Concentrate the reaction mixture under reduced pressure and purify by silica gel chromatography (ethyl acetate-hexane) to yield (S)-1-(4-bromo-phenyl)-3-((R)-1-phenyl-ethylamino)-5-(3-trifluoromethoxy-phenyl)-1,5-dihydro-pyrrol-2-one-eluting first (6.6 g, 36%): MS (m/z): 517.0 (M+1). RP HPLC: Tr=5.53 min (Method 3) and eluting second (R)-1-(4-bromo-phenyl)-3-((R)-1-phenyl-ethylamino)-5-(3-trifluoromethoxy-phenyl)-1,5-dihydro-pyrrol-2-one (5.8 g, 32%): MS (m/z): 517.0 (M+1). RP HPLC: Tr=5.44 min. (Method 3)

Workup

  1. concentrationConcentrate the reaction mixture under reduced pressure
  2. custompurify by silica gel chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-1e26e3cde2a742efb1f7c002eb8c921a
Source dataset
uspto-grants-2012_05
Patent number
US08168659B2

Reaction notes

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