Sodium Iodide → HCID 20605706, compound

HRID 497391Notes

Reaction equation

HRID 497391 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:12](=[O:14])[CH2:11][CH2:10][CH2:9][C:8]=2[N:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:6]=1)=[O:4].[Na+].[I-].C(N(CC)CC)C.[CH3:31][Si:32](Cl)([CH3:34])[CH3:33].C(=O)(O)[O-].[Na+]>CC#N>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:12]([O:14][Si:32]([CH3:34])([CH3:33])[CH3:31])=[CH:11][CH2:10][CH2:9][C:8]=2[N:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:6]=1)=[O:4]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 20605705HCID 20605705, compound

Product 1

HCID 20605706HCID 20605706, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-oxo-4,5,6,7-tetrahydro-indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (1.10 g, 3.74 mmol), NaI (841 mg, 5.61 mmol) and triethylamine (1.56 mL, 11.22 mmol) in CH3CN (15 mL), is added trimethylsilyl chloride (0.707 mL, 5.61 mmol) via syringe. The reaction mixture is stirred at room temperature for 15 h., 30 mL of ethyl acetate/hexanes (1:1 with a few drops of triethylamine) is added to dilute the solution. Saturated sodium bicarbonate solution (20 mL) is added. The layers are separated and the aqueous phase is extracted with ethyl acetate/hexanes (1:1) (3×10 mL). The combined organic layers are dried (Na2SO4) and evaporated to provide 4-trimethylsilanyloxy-6,7-dihydro-indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (1.3 g, 100%) as a viscous red oil.

Workup

  1. additionto dilute the solution
  2. customThe layers are separated
  3. extractionthe aqueous phase is extracted with ethyl acetate/hexanes (1:1) (3×10 mL)
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-663ab556b37f41288f1103f08f3ef0f8
Source dataset
uspto-grants-2005_09
Patent number
US06949562B2

Reaction notes

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