Tert-butyl4-(3-methyl-2-(phenylcarbamoyl)phenyl)-3-oxobutan-2-ylcarbamate → (S)-3-(1-aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one

HRID 1627215Notes

Reaction equation

HRID 1627215 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10](=O)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[C:19](=[O:27])[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:9])(C)(C)C>Cl.CO>[NH2:7][C@H:8]([C:10]1[N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:19](=[O:27])[C:13]2[C:12]([CH:11]=1)=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:18])[CH3:9]

Participants

3

Reactant 1

HCID 58008575Tert-butyl4-(3-methyl-2-(phenylcarbamoyl)phenyl)-3-oxobutan-2-ylcarbamate2×

Product 1

HCID 58008747(S)-3-(1-aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

Tert-Butyl 4-(3-methyl-2-(phenylcarbamoyl)phenyl)-3-oxobutan-2-ylcarbamate (compound 4703) (4.61 g, 0.012 mol) was dissolved in HCl/MeOH (50 mL) and stirred at reflux for 30 min. The mixture was concentrated in vacuo and then saturated Na2CO3 solution was added to adjust PH to about 7-8. The resulting solid was collected by filtration and further dried in vacuo to afford the desired product, 3-(1-aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one (compound 4704) (2.9 g, 90% yield, where the ratio of isomers is S:R=5:1) as a white solid.

Workup

  1. temperatureat reflux for 30 min
  2. concentrationThe mixture was concentrated in vacuo
  3. additionsaturated Na2CO3 solution was added
  4. filtrationThe resulting solid was collected by filtration
  5. customfurther dried in vacuo

Sources & evidence

ORD record
ord-34a8d2ce740e479f851cd62e6e1fae4b
Source dataset
uspto-grants-2014_07
Patent number
US08785456B2

Reaction notes

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