Citric Acid → (1H-indol-2-yl)methanol

HRID 2422216Notes

Reaction equation

HRID 2422216 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10](O)=[O:11].ON1C(=O)CCC1=O.Cl.C(N=C=NCCCN(C)C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[BH4-].[Na+]>O1CCCC1.CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][OH:11]

Participants

8

Reactant 5

HCID 311Citric Acid2×HCID 72899Indole-2-carboxylic acidHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 98783(1H-indol-2-yl)methanolYield 56%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of indole-2-carboxylic acid (2.0 g, 12 mmol), N,N-dimethylformamide (10 mL), tetrahydrofuran (20 mL) and N-hydroxysuccinimide (1.5 g, 13 mmol) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.9 g, 15 mmol), and the mixture was stirred overnight at room temperature. 0.5 M Aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated. Tetrahydrofuran (20 mL) and sodium tetrahydroborate (1.9 g, 50 mmol) were added to the residue under ice-cooling, and the mixture was stirred at room temperature for 6 hrs. 0.5 M Aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5:1) to give the title compound. yield 56%.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. temperaturecooling
  5. stirringthe mixture was stirred at room temperature for 6 hrs
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-e26506da4ac440b1858fd77713230323
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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