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

HRID 1243851
Notes
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Reaction equation

HRID 1243851 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2723640Glycine ethyl ester, hydrochlorideHCID 219286962-Chloro-5,5-diphenylcyclohexa-1,3-dienecarbaldehyde

Product 1

HCID 21929678ethyl 5,5-diphenyl-4,5-dihydro-2H-isoindole-1-carboxylateYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. temperatureThe reaction mixture is refluxed for about 20 hours
  2. concentrationthe mixture is concentrated to dryness under reduced pressure (13 kPa)
  3. washwashed with three times 50 cm3 of water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes