Glycine ethyl ester, hydrochloride → ethyl 5,5-diphenyl-4,5-dihydro-2H-isoindole-1-carboxylate

HRID 1243851Notes

Reaction equation

Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl[C:10]1[CH:15]=[CH:14][C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][C:11]=1[CH:28]=O>CN(C)C=O>[C:16]1([C:13]2([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:14]=[CH:15][C:10]3[C:11](=[CH:28][NH:2][C:3]=3[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:12]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 20 °C

Procedure

0.307 g of ethyl glycinate hydrochloride is added to a suspension of 0.589 g of 2-chloro-5,5-diphenylcyclohexa-1,3-dienecarbaldehyde in 20 cm3 of N,N-dimethylformamide. The reaction mixture is refluxed for about 20 hours. After cooling to a temperature in the region of 20° C., the mixture is concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 100 cm3 of ethyl acetate, washed with three times 50 cm3 of water and then dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure. After purification by flash chromatography on a column of silica [eluent: dichloromethane], 0.11 g of ethyl 5,5-diphenyl-4,5-dihydro-2H-isoindole-1-carboxylate is obtained in the form of a brown solid, the characteristics of which are as follows:

Workup

temperatureThe reaction mixture is refluxed for about 20 hours
concentrationthe mixture is concentrated to dryness under reduced pressure (13 kPa)
washwashed with three times 50 cm3 of water
dry with materialdried over magnesium sulphate
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure
customAfter purification by flash chromatography on a column of silica [eluent: dichloromethane]

Sources & evidence

ORD record: ord-9e8adcdf1d074219b18352a2d72b41b7
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119115B2

Reaction notes

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