Potassium Iodide → HCID 16663103, compound

HRID 548635Notes

Reaction equation

HRID 548635 reaction equation
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.[CH:6]1([CH2:12][NH:13][CH2:14][C@H:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:22][CH:21]=3)[C:18](=[O:36])[CH2:17][CH2:16]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[CH:6]1([CH2:12][N:13]([CH2:14][C@H:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][N:30]4[CH2:31][CH2:32][CH2:33][CH:34]4[CH3:35])=[CH:22][CH:21]=3)[C:18](=[O:36])[CH2:17][CH2:16]2)[CH2:2][CH:3]2[CH2:5][CH2:4]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 16058746HCID 16058746, compound

Product 1

HCID 16663103HCID 16663103, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

(Bromomethyl)cyclopropane a48 (47 μl, 0.48 mmol, 2.1 eq) is added to a solution of (5S)-5-{[(cyclohexylmethyl)amino]methyl}-1-[4-(3-piperidin-1-ylpropoxy)phenyl]pyrrolidin-2-one 2 in acetonitrile (4 ml), then cesium carbonate (150 mg, 0.46 mmol, 2 eq) and potassium iodide (8 mg, 0.05 mmol, 0.2 eq) are added and the mixture is heated at 50° C. for 24 h. The precipitate is filtered and the solvent is removed in vacuo. The residue is dissolved into dichloromethane and washed with a saturated solution of aqueous ammonium chloride. The aqueous layer is then extracted with dichloromethane, the organic layers are dried over magnesium sulfate and concentrated in vacuo to give 109 mg of a yellow oil. This oil is purified by chromatography over silicagel (dichloromethane/methanol/ammonia 92/8/0.8) to obtain 47 mg of (5S)-5-{[(cyclohexylmethyl)(cyclopropylmethyl)amino]methyl}-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}pyrrolidin-2-one 3 as a yellow oil.

Workup

  1. filtrationThe precipitate is filtered
  2. customthe solvent is removed in vacuo
  3. dissolutionThe residue is dissolved into dichloromethane
  4. washwashed with a saturated solution of aqueous ammonium chloride
  5. extractionThe aqueous layer is then extracted with dichloromethane
  6. dry with materialthe organic layers are dried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f5401e139bf4d468fb5aaa9b950ba89
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

Loading…