Hydrochloric Acid → HCID 86759900, compound

HRID 1063246Notes

Reaction equation

HRID 1063246 reaction equation
C(OC([N:11]1[CH2:23][CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:27][CH:26]=3)[C:13]=2[CH2:12]1)=O)C1C=CC=CC=1.[ClH:35]>CO.O1CCOCC1.[Pd]>[ClH:35].[C:32]([CH2:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]3[CH2:22][CH2:23][NH:11][CH2:12][C:13]2=3)=[CH:26][CH:27]=1)([OH:34])=[O:33]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 22278940HCID 22278940, compound

Product 1

HCID 86759900HCID 86759900, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-benzyloxycarbonyl-9-{[4-(carboxymethyl)phenyl]methyl}-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole (6.91 g, 15.22 mmole) in methanol (50 mL), dioxane (50 mL) and HCl (19 mL, 1M in dioxane) at RT in a Parr hydrogenation flask was added 10% Pd/C (0.5 g). The reaction mixture was shaken under 45 psi of H2 for 6 hr. The suspension was filtered through celite®, and the filter pad was washed with methanol. The filtrate was concentrated on the rotavap, and the residue was dried under high vacuum to afford the titled compound (5.22 g, 90%) as a white solid: MS (ES) m/e 345 (M+H−HCl)+.

Workup

  1. filtrationThe suspension was filtered through celite®
  2. washthe filter pad was washed with methanol
  3. concentrationThe filtrate was concentrated on the rotavap
  4. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-7818c56575d840d0bbf966f19d1a0453
Source dataset
uspto-grants-2005_11
Patent number
US06964970B2

Reaction notes

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