Hydrogen Peroxide → 1-t-Butoxycarbonyl-2-methylindole-4-acetic Acid

HRID 11401Notes

Reaction equation

HRID 11401 reaction equation
C1CCCCC1.[C:7]([O:11][C:12]([N:14]1[C:22]2[C:17](=[C:18]([C:23]#[C:24][Si](C)(C)C)[CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[CH3:29])=[O:13])([CH3:10])([CH3:9])[CH3:8].[OH-:30].[Na+].[OH:32]O>O1CCCC1>[C:7]([O:11][C:12]([N:14]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:23][C:24]([OH:32])=[O:30])[C:17]=2[CH:16]=[C:15]1[CH3:29])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8078CyclohexaneHCID 14798Sodium HydroxideHCID 219743931-t-Butoxycarbonyl-2-methyl-4-(2-trimethylsilylethynyl)indole

Product 1

HCID 219744891-t-Butoxycarbonyl-2-methylindole-4-acetic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of cyclohexane (16.1 ml) in tetrahydrofuran (160 ml) was cooled at −10° C., and then to the mixture was added dropwise borane-tetrahydrofuran complex (1M, 80 ml), and the mixture was stirred at 0° C. for 1 hour. To the solution was added dropwise a solution of 1-t-butoxycarbonyl-2-methyl-4-(2-trimethylsilylethynyl)indole (13.1 g; prepared in Reference Example 3) in tetrahydrofuran (60 ml), the mixture was stirred for 1 hour at room temperature. To a reaction solution was added dropwise 3N aqueous solution of sodium hydroxide (40 ml) and 30% hydrogen peroxide (in water, 45 ml), successively, and the mixture was stirred for 12 hours. The reaction mixture was extracted with water-diethyl ether. The aqueous layer was adjusted to acidic condition with hydrochloric acid and then extracted with ethyl acetate. The extraction was washed with water and a saturated aqueous solution of sodium chloride, successively, dried and concentrated under reduced pressure to give the title compound (10.4 g; crude).

Workup

  1. additionto the mixture was added dropwise borane-tetrahydrofuran complex (1M, 80 ml)
  2. stirringthe mixture was stirred for 1 hour at room temperature
  3. stirringsuccessively, and the mixture was stirred for 12 hours
  4. extractionThe reaction mixture was extracted with water-diethyl ether
  5. extractionextracted with ethyl acetate
  6. extractionThe extraction
  7. washwas washed with water
  8. dry with materiala saturated aqueous solution of sodium chloride, successively, dried
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b28a894c0a8745c8aa52e46ff1d2c3dd
Source dataset
uspto-grants-2006_08
Patent number
US07098234B2

Reaction notes

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