1-Carbomethoxy-2-benzylamino-3,4-dihydronaphthalene → cis 1-Carbomethoxy-2-amino-1,2,3,4-tetrahydronaphthalene

HRID 1350193Notes

Reaction equation

HRID 1350193 reaction equation
[C:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]=1[NH:15]CC1C=CC=CC=1)([O:3][CH3:4])=[O:2]>CO.[Pd]>[C:1]([C@@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C@@H:6]1[NH2:15])([O:3][CH3:4])=[O:2]

Participants

4

Reactant 1

HCID 210946731-Carbomethoxy-2-benzylamino-3,4-dihydronaphthalene

Product 1

HCID 58646756cis 1-Carbomethoxy-2-amino-1,2,3,4-tetrahydronaphthaleneYield 15.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 1-carbomethoxy-2-benzylamino-3,4-dihydronaphthalene (1.46 g) in methanol (30 mL) at room temperature, was added 10% palladium on carbon (200 mg). The resulting mixture was shaken under a hydrogen atmosphere at 40 psi for 3 d using a Parr apparatus. The catalyst was filtered, and the filtrate was evaporated under vacuum to obtain crude product. The crude product was purified by reverse phase preparative HPLC to obtain predominantly cis 1-carbomethoxy-2-amino-1,2,3,4-tetrahydronaphthalene (160 mg) as a cis-trans mixture (10:1).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate was evaporated under vacuum
  3. customto obtain crude product
  4. customThe crude product was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-5df5577a07544c31ad34fcc1d73bbb91
Source dataset
uspto-grants-2007_05
Patent number
US07214704B2

Reaction notes

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