1-Aminomethyl-3-cyclohexyl-5,6-dimethoxy-3,4-dihydronaphthalene hydrochloride → [1R,3S]1-Aminomethyl-3-cyclohexyl-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene Hydrochloride

HRID 54133Notes

Reaction equation

HRID 54133 reaction equation
[ClH:1].[NH2:2][CH2:3][C:4]1[C:13]2[C:8](=[C:9]([O:16][CH3:17])[C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[CH2:7][CH:6]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:5]=1.[H][H]>C(O)C.[Pd]>[ClH:1].[NH2:2][CH2:3][C@H:4]1[C:13]2[C:8](=[C:9]([O:16][CH3:17])[C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[CH2:7][C@@H:6]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:5]1

Participants

5

Reactant 2

HCID 199611061-Aminomethyl-3-cyclohexyl-5,6-dimethoxy-3,4-dihydronaphthalene hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 18641645[1R,3S]1-Aminomethyl-3-cyclohexyl-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene HydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

1-Aminomethyl-3-cyclohexyl-5,6-dimethoxy-3,4-dihydronaphthalene hydrochloride (1 g, 3.3 mmol), from Step 2 of Example 36, was dissolved in 20 mL of ethanol and 0.25 g of 10% palladium on carbon was added to the ethanol solution. The reaction mixture was sealed under one atmosphere of hydrogen and shaken at ambient temperature for 24 h. The reaction mixture was filtered to remove the catalyst and concentrated to give 1 g (100% yield) of the title compound, m.p. 282°-283° C.; 1H NMR (d6 -DMSO) δ: 1.0-1.5 (m, 8H), 1.5-1.9 (m, 5H), 2.0-2.2 (m, 2H), 2.7-3.1 (m, 3H), 3.3-3.4 (m, 1H), 3.8 (s, 3H), 3.9 (s, 3H), 6.4-6.8 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-10a43f8d0b644f44a136e5aeef043f81
Source dataset
uspto-grants-1997_04
Patent number
US05621133

Reaction notes

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