Sodium Iodide → HCID 20605706, compound

HRID 481072Notes

Reaction equation

HRID 481072 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. 1H NMR (400 MHz, CDCl3) δ0.180 (9H, s), 1.576 (9H, s), 2.343 (2H, m), 2.930 (2H, t), 3.781 (3H, s), 4.826 (1H, t), 7.580 (1H, s). MS (ES+) 366 (M+1)

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-4dc88dd3e24841eeb55575314a04756a
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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