HCID 20714572, compound → HCID 20714574, compound

HRID 1078073Notes

Reaction equation

HRID 1078073 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C@@H:12]([CH2:14][OH:15])[C@@H:11]([NH:16][CH2:17][CH:18]=[CH2:19])[CH2:10][CH2:9]2.[H][H]>[Pd].C(O)C>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C@@H:12]([CH2:14][OH:15])[C@@H:11]([NH:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH2:9]2

Participants

5

Reactant 2

HCID 20714572HCID 20714572, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20714574HCID 20714574, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The mixture of 0.99 g (4.0 mmol) of cis-(+-)-1,2,3,4-tetrahydro-8-methoxy-2-(2-propenylamino)-1-naphthalenemethanol hydrochloride, 0.5 g 10% Palladium on carbon, and 80 mL of 95% ethanol was shaken in a Parr shaker apparatus under 50 p.s.i. of hydrogen atmosphere. After 18 hours, the mixture was filtered through a Celite pad, concentrated in vacuo. The resulting oil was treated with excess HCl/MeOH and recrystallized from ethyl acetate/methanol to give pure title compound as a white solid: m.p. 233°-234° C.

Workup

  1. filtrationthe mixture was filtered through a Celite pad
  2. concentrationconcentrated in vacuo
  3. additionThe resulting oil was treated with excess HCl/MeOH
  4. customrecrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-bc0cc69c8e234504b59a6f2030dd33e7
Source dataset
uspto-grants-1996_08
Patent number
US05545755

Reaction notes

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