Water → HCID 178432842, compound

HRID 1625525Notes

Reaction equation

HRID 1625525 reaction equation
[CH3:1][CH:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]2[NH:15][CH:16]=[C:17]([CH3:19])[N:18]=2)[CH2:3]1.[I:20]N1C(=O)CCC1=O.O>C(Cl)Cl>[I:20][C:16]1[NH:15][C:14]([C@@H:4]2[CH2:3][C@H:2]([CH3:1])[CH2:6][N:5]2[C:7]([O:9][C:10]([CH3:13])([CH3:11])[CH3:12])=[O:8])=[N:18][C:17]=1[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 178430877HCID 178430877, compound

Product 1

HCID 178432842HCID 178432842, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl (2S)-4-methyl-2-(4-methyl-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (307 mg, 1.013 mmol) in CH2Cl2 (15 mL) is added N-iodosuccinimide (240 mg, 1.013 mmol) at 5° C. The reaction mixture is stirred for one hour and water (2 mL) is added. The organic layer is separated, dried over Na2SO4, and evaporated to dryness. The residue is purified by flash column chromatography on silica gel (12 to 100% EtOAc in Hexanes) to give tert-butyl (2S,4S)-2-(5-iodo-4-methyl-1H-imidazol-2-yl)-4-methyl-pyrrolidine-1-carboxylate (246 mg, 62%).

Workup

  1. customThe organic layer is separated
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. customThe residue is purified by flash column chromatography on silica gel (12 to 100% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-9df6260255574e639e2f4cea78a7bccf
Source dataset
uspto-grants-2014_07
Patent number
US08779156B2

Reaction notes

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