Hydrochloric Acid → HCID 13711372, compound

HRID 1732141Notes

Reaction equation

HRID 1732141 reaction equation
C(OC([N:11]1[C@H:23]([CH2:24][C:25]([OH:27])=[O:26])[CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH2:12]1)=O)C1C=CC=CC=1.[ClH:28]>C(O)C.[H][H].[Pd]>[ClH:28].[CH2:12]1[C:13]2[NH:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]=2[CH2:22][C@@H:23]([CH2:24][C:25]([OH:27])=[O:26])[NH:11]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 13863922HCID 13863922, compound

Product 1

HCID 13711372HCID 13711372, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

0.55 g of (3S)-2-benzyloxycarbonyl-1,2,3,4-tetrahydro-β-carboline-3-acetic acid is dissolved in 12 ml of 80% aqueous ethanol. 0.5 g of 10% Pd-C and 3 ml of 10% HCl are added to the solution. The mixture is subjected to catalytic reduction in hydrogen gas under atmospheric pressure at room temperature. The catalyst is filtered off, and washed with ethanol. The filtrate and the washings are combined, and evaporated to remove the solvent. The residue is recrystallized from ethyl acetate. 290 mg of (3S)-1,2,3,4-tetrahydro-β-carboline-3-acetic acid hydrochloride are obtained as pale yellow needles. Yield: 72%

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with ethanol
  3. customevaporated
  4. customto remove the solvent
  5. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c970592f427242c6887495fc8980f61e
Source dataset
uspto-grants-1986_11
Patent number
US04625032

Reaction notes

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