N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine → 2,3-Dihydroxybutanedioic Acid

HRID 2211338Notes

Reaction equation

HRID 2211338 reaction equation
[C@@H:1]([OH:10])([C:7]([OH:9])=[O:8])[C@H:2]([OH:6])[C:3]([OH:5])=[O:4].CNC1C2C(=CC=CC=2)CCC1>O>[C:7]([OH:9])(=[O:8])[CH:1]([CH:2]([C:3]([OH:5])=[O:4])[OH:6])[OH:10]

Participants

4

Reactant 2

HCID 46475N-methyl-1,2,3,4-tetrahydronaphthalen-1-amineHCID 439655D-Tartaric acid

Product 1

HCID 8752,3-Dihydroxybutanedioic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (2S,3S) (-) tartaric acid (160.3 g in water (50 ml) was treated with N-methyl-1,2,3,4-tetrahydro-1-naphthylamine (172.2 g), the temperature being allowed to rise to 35° C. The resulting clear solution was chilled to induce crystallisation and granulated for several hours at 5° C. Filtration, washing with water (3×50 ml) and drying gave the crude (-) tartaric acid salt of the (S)-amine (198.2 g) as a white solid, m.p. 99°-106° C. Fractional recrystallisation from water gave the (-)tartaric acid salt of the title compound (59.3 g, 33.7% overall based on available enantiomer) as white crystals, m.p. 107°-109° C., [α]D -12.4° (c=4.96, water). Found: C,54.82; H,7.09; N,4.21. C15H21NO6 ;H2O requires C,54.70; H,7.04; N,4.25%.

Workup

  1. customto rise to 35° C
  2. temperatureThe resulting clear solution was chilled
  3. customcrystallisation
  4. waitgranulated for several hours at 5° C
  5. filtrationFiltration
  6. washwashing with water (3×50 ml)
  7. customdrying

Sources & evidence

ORD record
ord-2714cc5dc63848249aa655a9ed2170ce
Source dataset
uspto-grants-1995_10
Patent number
US05463126

Reaction notes

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