HCID 17815508, compound → HCID 17815681, compound

HRID 1373222Notes

Reaction equation

HRID 1373222 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[O:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=2[N+:26]([O-])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[C].[Pd].C(OCC)(=O)C>[NH2:26][C:20]1[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=1[O:18][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH2:16][CH2:17][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:9]2

Participants

4

Reactant 1

HCID 17815508HCID 17815508, compound

Product 1

HCID 17815681HCID 17815681, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5% carbon-palladium (1.3 g) was added to an ethyl acetate (100 ml) solution of 2-tert-butoxycarbonyl-5-(5-chloro-2-nitrophenoxy)-1,2,3,4-tetrahydroisoquinoline (4.25 g, 10.5 mmols). The resulting mixture was hydrogenated at room temperature under atmospheric pressure. The catalyst was removed through filtration, and the filtrate was concentrated under reduced pressure. The residue was purified through silica gel column chromatography to give an oil of 5-(2-amino-5-chlorophenoxy)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinoline (2.95 g, 75%).

Workup

  1. customwas hydrogenated at room temperature under atmospheric pressure
  2. customThe catalyst was removed through filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-dc2f31f90bbf4ea58430dc03228c89fd
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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