Methyl iodide → Methyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-1-methyl-2-indolyl)propionate

HRID 361918Notes

Reaction equation

HRID 361918 reaction equation
C(O[N:6]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH2:23][C:24]3[NH:25][C:26]4[C:31]([CH:32]=3)=[CH:30][C:29]([C:33]#[N:34])=[CH:28][CH:27]=4)[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=2)[C:7]1=C=O)(C)(C)C.[H-].[Na+].[CH3:39]I.[C:41]1([CH3:47])[CH:46]=CC=C[CH:42]=1.[C:48]([O:51]CC)(=[O:50])C>CN(C)C=O>[C:41]([O:51][C:48]([N:6]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH2:23][C:24]3[N:25]([CH3:39])[C:26]4[C:31]([CH:32]=3)=[CH:30][C:29]([C:33]#[N:34])=[CH:28][CH:27]=4)[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=2)[CH2:7]1)=[O:50])([CH3:47])([CH3:46])[CH3:42]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21584019Toluene ethylacetateHCID 86750715methyl 2-[4-[((3S)-1-tert-butoxy-carbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-2-indolyl)propionate

Product 1

HCID 57060150Methyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-1-methyl-2-indolyl)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.0 g of methyl 2-[4-[((3S)-1-tert-butoxy-carbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-2-indolyl)propionate was dissolved in 30 ml of N,N-dimethyl-formamide, and then stirred under ice cooling. 270 mg of 60% sodium hydride was added to the above solution, and the stirring was continued for 10 minutes. The resulting reaction solution was mixed with 0.4 ml of methyl iodide, and the mixture was stirred at room temperature for 1 hour. The thus treated reaction solution was diluted with a toluene/ethyl acetate mixture, and then washed with an aqueous solution of ammonium chloride. After drying the resulting organic layer to distill off the solvent, the residue thus obtained was purified by subjecting it to silica gel column chromatography using a dichloromethane/acetone mixture as an elution solvent. In this way, 2.0 g of the title compound was obtained in a viscous and oily form.

Workup

  1. customThe resulting reaction solution
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. customThe thus treated reaction solution
  4. washwashed with an aqueous solution of ammonium chloride
  5. customAfter drying the resulting organic layer
  6. distillationto distill off the solvent
  7. customthe residue thus obtained
  8. customwas purified

Sources & evidence

ORD record
ord-827a8fb90f31429bb6bb358169bcb5fa
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Reaction notes

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