1-Aminomethyl-5-methoxy-3-phenyl-3,4-dihydronaphthalene hydrochloride → [1R,3S] 1-aminomethyl-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene hydrochloride

HRID 982095Notes

Reaction equation

HRID 982095 reaction equation
[ClH:1].[NH2:2][CH2:3][C:4]1[C:13]2[C:8](=[C:9]([O:14][CH3:15])[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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:14][CH3:15])[CH:10]=[CH:11][CH:12]=2)[CH2:7][C@@H:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5]1

Participants

5

Reactant 2

HCID 200690961-Aminomethyl-5-methoxy-3-phenyl-3,4-dihydronaphthalene hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 67931190[1R,3S] 1-aminomethyl-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene hydrochlorideYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 0.22 g (0.73 mmol) of 1-aminomethyl-5-methoxy-3-phenyl-3,4-dihydronaphthalene hydrochloride, from Step 2, of Example 2, in 5 mL of absolute ethanol, was added 0.05 g of 10% palladium supported on carbon. The reaction mixture was sealed under a blanket of hydrogen and stirred overnight at ambient temperature. The reaction mixture was flushed with nitrogen before it was filtered through Celite filter aid and washed with 15 mL of absolute ethanol and 15 mL of methylene chloride. The filtrate was concentrated to give 0.16 g (79% yield) of [1R,3S] 1-aminomethyl-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene hydrochloride, m. p. 235°-237° C.; 1H NMR (d6-DMSO) δ2.15-2.25 (m, 2H), 2.5-2.65 (m, 1H), 2.8-2.95 (m, 2H), 3.0-3.1 (m, 1H), 3.1-3.4 (m, 1H), 3.45-3.5 (m, 1H), 3.72 (s, 3H), 6.43 (d, 1H), 6.62 (d, 1H), 6.94 (t, 1H), 7.2-7.3 (m, 1H), 7.35-7.45 (m, 4H).

Workup

  1. customThe reaction mixture was flushed with nitrogen before it
  2. filtrationwas filtered through Celite
  3. filtrationfilter aid
  4. washwashed with 15 mL of absolute ethanol and 15 mL of methylene chloride
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-950cda6b1d824e0cb8855d6439aae712
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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