(S,E)-tert-butyl 4-(4-(5,6-dichloro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)styryl)-2,2-dimethyloxazolidine-3-carboxylate → (S)-tert-butyl 4-(4-(5,6-dichloro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)phenethyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 1805245Notes

Reaction equation

HRID 1805245 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:14]1[CH:35]=[CH:34][C:17](/[CH:18]=[CH:19]/[C@H:20]3[CH2:24][O:23][C:22]([CH3:26])([CH3:25])[N:21]3[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:16][CH:15]=1)[C:7]2=[O:13]>CO.[Pt]>[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:14]1[CH:35]=[CH:34][C:17]([CH2:18][CH2:19][C@H:20]3[CH2:24][O:23][C:22]([CH3:26])([CH3:25])[N:21]3[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:16][CH:15]=1)[C:7]2=[O:13]

Participants

4

Reactant 1

HCID 67151848(S,E)-tert-butyl 4-(4-(5,6-dichloro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)styryl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 67151682(S)-tert-butyl 4-(4-(5,6-dichloro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)phenethyl)-2,2-dimethyloxazolidine-3-carboxylateYield 75.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

To a stirred suspension of (S,E)-tert-butyl 4-(4-(5,6-dichloro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)styryl)-2,2-dimethyloxazolidine-3-carboxylate (220 mg) in methanol (8 ml) was added 10% platinum on charcoal (42 mg) and the mixture was then stirred under an atmosphere of hydrogen at room temperature for 2 hours. The mixture was then filtered through celite and the filtrate was concentrated in vacuo to afford (S)-tert-butyl 4-(4-(5,6-dichloro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)phenethyl)-2,2-dimethyloxazolidine-3-carboxylate (166 mg, 75%) as a white amorphous solid. MS (ISP): 538.3 ([{37Cl35Cl}M+NH4]+), 536.2 ([{35Cl}M+NH4]+), 521.3 ([{37Cl35Cl}M+H]+), 519.2 ([{35Cl}M+H]+), 465.3 ([{37Cl35Cl}M+H—C4H8]+), 463.1 ([{35Cl}M+H—C4H8]+).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8558668fd22c4c36b510f545ebfe63b4
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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