7-Chloro-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one → (S)-7-Chloro-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one

HRID 2427605Notes

Reaction equation

HRID 2427605 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[CH3:13])[CH2:7]2>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([C@H:12]([C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1)[CH3:13])[CH2:7]2.[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([C@@H:12]([C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1)[CH3:13])[CH2:7]2

Participants

4

Reactant 1

HCID 579497997-Chloro-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one

Product 2

HCID 57949417(S)-7-Chloro-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-oneHCID 57949812(R)-7-Chloro-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Chromatography (HPLC) of racemic mixture of 7-chloro-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one (1.2 g) through ChrialCel OD (250×20 mm i.d., 10 μm)] using 5% isopropyl alcohol in hexanes as an eluent afforded (S)-7-Chloro-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one (0.044 g) and (R)-7-Chloro-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one (0.058 g)

Sources & evidence

ORD record
ord-879f3e632f3c482dbb82ce9359922eba
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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