cis-2-Azido-6-methoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene → cis-1,2,3,4-Tetrahydro-6-methoxy-1-phenyl-2-naphthalenamine

HRID 370015Notes

Reaction equation

HRID 370015 reaction equation
[N:1]([C@H:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH3:15])[CH:10]=2)[C@H:5]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[N+]=[N-]>C(O)(C)C.[Pd]>[CH3:15][O:14][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C@@H:5]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@@H:4]([NH2:1])[CH2:13][CH2:12]2

Participants

4

Reactant 1

HCID 53966566cis-2-Azido-6-methoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 53926786cis-1,2,3,4-Tetrahydro-6-methoxy-1-phenyl-2-naphthalenamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

The azido-tetrahydronaphthalene 31 obtained above (1.3 g) was dissolved in isopropanol (50 mL) and this solution was hydrogenated at 50 psi over 10% palladium on carbon (0.2 g) at room temperature for 18 h. The catalyst was removed by filtration and the solvent was evaporated in vacuo to afford crude cis-1,2,3,4-tetrahydro-6-methoxy-1-phenyl-2-naphthalenamine 32 as an oil, which was used in the subsequent step without purification (FIG. 10). MS m/e (MH+) 254.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-5b5b7e19d2ca470196af68ba526ddd11
Source dataset
uspto-grants-2000_10
Patent number
US06140354

Reaction notes

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