HCID 19961156, compound → HCID 18641652, compound

HRID 1089014Notes

Reaction equation

HRID 1089014 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]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH: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]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:5]1

Participants

5

Reactant 2

HCID 19961156HCID 19961156, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18641652HCID 18641652, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 0.2 g (0.67 mmol) of 1 aminomethyl 3,4-dihydro-5,6-dimethoxy-3-phenyl naphthalene 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 0.2 g (100% yield) of [1R,3S]1-aminomethyl-5,6-dimethoxy-3-phenyl 1,2,3,4-tetrahydro-naphthalene hydrochloride, m.p. 230°-231° C. 1H NMR (d6 -DMSO) delta 2.15-2.25 (m, 1H), 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, 1 H), 3.66 (s, 3H), 3.78 (s, 3H), 6.95 (d, 1H), 7.12 (d, 1H), 7.2-7.3 (m, 1H), 7.35-7.45 (m, 4H), 8.0 (br s, 3H).

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-ef92c9062e7347eaa72393a20873cf87
Source dataset
uspto-grants-1990_10
Patent number
US04963568

Reaction notes

Loading…