Benzyl 1-tert-butoxycarbonylindole-4-carboxylate → 1-Boc-4-carboxyindole

HRID 2389338Notes

Reaction equation

HRID 2389338 reaction equation
[N:1]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12]CC3C=CC=CC=3)=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H][H]>[Pd].CO.O>[C:23]([O:22][C:20]([N:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([OH:12])=[O:11])[C:4]=2[CH:3]=[CH:2]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 2

HCID 53760164Benzyl 1-tert-butoxycarbonylindole-4-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 497588501-Boc-4-carboxyindoleYield 61.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The mixture of 4-benzyl 1-tert-butyl 1H-indole-1,4-dicarboxylate (6.37 g) and 10% palladium on carbon (964 mg) in MeOH (95.6 mL) and water (3.2 mL) was hydrogenated at 3.5 atm of hydrogen for 3.5 hours. The resulting mixture was filtered through a bed of celite and the filtrate was evaporated in vacuo. The residue was dissolved in chloroform (100 mL) and the solution was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was triturated with cold MeOH (20 mL) to give 1-(tert-butoxycarbonyl)-1H-indole-4-carboxylic acid (2.90 g) as a colorless crystals. The above filtrate was evaporated in vacuo and the residue was triturated with solvent (n-hexane:EtOAc=5:1, 12 mL) to afford 1-(tert-butoxycarbonyl)-1H-indole-4-carboxylic acid (1.31 g) as colorless crystals.

Workup

  1. filtrationThe resulting mixture was filtered through a bed of celite
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in chloroform (100 mL)
  4. dry with materialthe solution was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was triturated with cold MeOH (20 mL)

Sources & evidence

ORD record
ord-b1333f2b2012457e9ad42c88bd177291
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

Loading…