Hydrochloric Acid → D-1,2,3,4-Tetrahydronorharman-3-carboxylic acid

HRID 373110

Reaction equation

HRID 373110 reaction equation
[NH2:1][C@@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[OH-].[Na+].[CH2:18]=O.Cl>O>[CH2:18]1[C:5]2[NH:6][C:7]3[C:12]([C:4]=2[CH2:3][C@H:2]([C:13]([OH:15])=[O:14])[NH:1]1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 9060D-TryptophanHCID 14798Sodium Hydroxide

Product 1

HCID 675102D-1,2,3,4-Tetrahydronorharman-3-carboxylic acidYield 87.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

20.0 g D-tryptophan is suspended in 40 ml of water and 7.83 g 50%(w/w) sodium hydroxide solution is added and this mixture is stirred to give a clear solution. 7.95 g 37% formaldehyde is added and this mixture is stirred for 2 hours at room temperature, then refluxed for 3 hours. The hot solution is poured into 200 ml water and, with vigorous stirring, the pH is adjust to 5 with 6N hydrochloric acid, giving a precipitate. The slurry is stirred for 18 hours, filtered, and the solid dried at 70° C./0.1 mm Hg overnight to give 18.5 g (3R)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid.

Workup

  1. customto give a clear solution
  2. stirringthis mixture is stirred for 2 hours at room temperature
  3. temperaturerefluxed for 3 hours
  4. customgiving a precipitate
  5. stirringThe slurry is stirred for 18 hours
  6. filtrationfiltered
  7. customthe solid dried at 70° C./0.1 mm Hg overnight

Sources & evidence

ORD record
ord-265860efbbbd464a9f4f85ffc7463a62
Source dataset
uspto-grants-1992_11
Patent number
US05162336

Linked notes

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