Ethyl Acetate → HCID 67252332, compound

HRID 2427551Notes

Reaction equation

HRID 2427551 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.C[O:12][C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20]Br.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:10]2[CH2:20][C:15]3[C:14](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:13]2=[O:12])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 978031-(4-Chlorophenyl)ethylamineHCID 2734813Methyl 2-(bromomethyl)benzoate

Product 1

HCID 67252332HCID 67252332, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(4-chlorophenyl)-ethylamine (117 mg (0.75 mmol), 2-bromomethyl-benzoic acid methyl ester (172 mg, 0.75 mmol), and K2CO3 (207 mg, 1.5 mmol) in toluene (5 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using a gradient of hexanes to ethyl acetate afforded 38 mg of 2-[1-(4-chlorophenyl)-ethyl]-2,3-dihydroisoindol-1-one, as the racemic mixture. Chromatography (HPLC) of this material through ChrialCel OD (250×20 mm i.d., 10 μm) using 5% isopropanol in hexanes afforded 11.6 mg of R-2-[1-(4-chlorophenyl)-ethyl]-2,3-dihydro-isoindol-1-one and 8.3 mg of S-2-[1-(4-chlorophenyl)-ethyl]-2,3-dihydro-isoindol-1-one. GC/MS for S-2-[1-(4-chlorophenyl)-ethyl]-2,3-dihydroisoindol-1-one gave: m/z (rel.int.) 274 (M+, 9), 272 (M+, 56), 258 (26), 256 (57), 160 (20), 138 (32), 119 (100), 103 (50), 91 (65), and 77 (61).

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-4da25d41db3b47109d10c97d4fec8eab
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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