HCID 13863935, compound → HCID 13653080, compound

HRID 1732135Notes

Reaction equation

HRID 1732135 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C@H:4]([CH2:6][C:7]1[C:15]2[C:10](=[C:11]([CH3:16])[CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5].Cl.[CH3:19]O>CO>[CH3:16][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[NH:9][C:8]1[CH2:19][NH:5][C@H:4]([C:3]([O:2][CH3:1])=[O:17])[CH2:6][C:7]2=1

Participants

4

Reactant 2

HCID 13863935HCID 13863935, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 13653080HCID 13653080, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.02 g of 7-methyl-L-tryptophan methyl ester are dissolved in 20 ml of methanol, and 4 ml of 15% HCl-methanol are added thereto. The mixture is evaporated to remove the solvent. The residue is dissolved in 30 ml of methanol, and 2.86 g of 35% formalin are added thereto. The mixture is stirred at room temperature overnight. The mixture is evaporated to remove the solvent, and water is added to the residue. The aqueous solution is adjusted to pH 10 with 10% aqueous ammonia, and extracted with ethyl acetate. The extract is washed with water, dried and then evaporated to remove the solvent. The residue is recrystallized from chloroform. 2.0 g of methyl (3S)-8-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate are obtained as pale yellow prisms. Yield: 63%

Workup

  1. customThe mixture is evaporated
  2. customto remove the solvent
  3. dissolutionThe residue is dissolved in 30 ml of methanol
  4. addition2.86 g of 35% formalin are added
  5. customThe mixture is evaporated
  6. customto remove the solvent, and water
  7. additionis added to the residue
  8. extractionextracted with ethyl acetate
  9. washThe extract is washed with water
  10. customdried
  11. customevaporated
  12. customto remove the solvent
  13. customThe residue is recrystallized from chloroform

Sources & evidence

ORD record
ord-8cdb0c1172c745ba91d4914420bfba8d
Source dataset
uspto-grants-1986_11
Patent number
US04625032

Reaction notes

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