Octanal → (3R)-1,2,3,4-Tetrahydro-1-heptyl-beta-carboline-3-carboxylic Acid

HRID 361560

Reaction equation

HRID 361560 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.S(=O)(=O)(O)O.C(O)C.[CH:24](=O)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>CO>[CH2:25]([CH:24]1[C:5]2[NH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]=2[CH2:3][C@H:2]([C:13]([OH:15])=[O:14])[NH:1]1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 454OctanalHCID 702EthanolHCID 1118Sulfuric AcidHCID 9060D-Tryptophan

Product 1

HCID 54381401(3R)-1,2,3,4-Tetrahydro-1-heptyl-beta-carboline-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

A mixture containing 147 mmol of D-tryptophan, 294 ml of 1 N sulfuric acid, 300 ml of ethanol and 294 mmol of octanal is stirred at 45° C. for 72 hours. The solution is concentrated and the residue is taken up in a water/methanol/ammonium hydroxide mixture. The methanol is evaporated at 45° C. and the precipitate is filtered off, washed with water and dried. The solid obtained is solubilized at high temperature in methanol. After cooling, the compound of preparation F crystallizes. It is then filtered and dried.

Workup

  1. concentrationThe solution is concentrated
  2. customThe methanol is evaporated at 45° C.
  3. filtrationthe precipitate is filtered off
  4. washwashed with water
  5. customdried
  6. customThe solid obtained
  7. temperatureAfter cooling
  8. customthe compound of preparation F
  9. customcrystallizes
  10. filtrationIt is then filtered
  11. customdried

Sources & evidence

ORD record
ord-de5d6c05f5a346829f1503e4c3bf2084
Source dataset
uspto-grants-1999_02
Patent number
US05866587

Linked notes

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