7-Methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid → HCID 39098232, compound

HRID 218556Notes

Reaction equation

HRID 218556 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]2[C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1>CO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C@@H:10]2[C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 132774847-Methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid

Product 1

HCID 39098232HCID 39098232, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (5.0 g) and (S)-(−)-1-phenethylamine (3.2 mL) were dissolved in methanol (50 mL), and the solvent was evaporated under reduced pressure to give crude crystals (7.33 g). This was recrystallized from a mixed solvent of methanol and isopropyl ether. The obtained crystals were partitioned between ethyl acetate and 1 mol/L-hydrochloric acid. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give (S)-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (0.96 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customto give crude crystals (7.33 g)
  3. customThis was recrystallized from a mixed solvent of methanol and isopropyl ether
  4. customThe obtained crystals were partitioned between ethyl acetate and 1 mol/L-hydrochloric acid
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ab66b2a2ac1d4aefb04acdcfc368a850
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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