Iodine → HCID 11857597, compound

HRID 1710744Notes

Reaction equation

HRID 1710744 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:20][CH:21]=[C:22]([CH2:24][C:25](=O)[N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[N:23]=2)=[CH:15][CH:14]=1.II.[OH-].[K+]>O1CCCC1.CO>[CH3:3][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[O:20][CH:21]=[C:22]([CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[N:23]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 4311764Sodium borohydrideHCID 11857527HCID 11857527, compound

Product 1

HCID 11857597HCID 11857597, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of sodium borohydride (0.05 g, 1.21 mmol, 2.4 eq) in tetrahydrofuran (0.5 ml) is added a solution of 2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-4-(2-oxo-2-pyrrolidin-1-ylethyl)-1,3-oxazole 52 (0.2 g, 0.5 mmol, 1 eq) in tetrahydrofuran (2 ml). The mixture is cooled down to 0° C. (ice bath) and a solution of iodine (0.13 g, 0.5 mmol, 1 eq) in tetrahydrofuran (1 ml) is added dropwise. When the release of gas has stopped, the mixture is heated to reflux overnight. Methanol is added to the mixture at 0° C. until complete dissolution. The solvent is removed under vacuum to give a white solid. The solid is taken up into a 20% methanolic solution of potassium hydroxide and the mixture is heated at 60° C. for 10 h. The mixture is poured onto water and extracted with dichloromethane. The organic layer is dried over magnesium sulfate and the solvent is removed in vacuum. The crude product is purified by chromatography over silica gel (eluent: gradient of dichloromethane/methanol/ammonia) to give 0.03 g of 2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole 55 as an orange oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux overnight
  3. customThe solvent is removed under vacuum
  4. customto give a white solid
  5. temperaturethe mixture is heated at 60° C. for 10 h
  6. additionThe mixture is poured onto water
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic layer is dried over magnesium sulfate
  9. customthe solvent is removed in vacuum
  10. customThe crude product is purified by chromatography over silica gel (eluent: gradient of dichloromethane/methanol/ammonia)

Sources & evidence

ORD record
ord-d1c2aa073375451c8eae933bb2c111c9
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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