Sodium Iodide → HCID 57656859, compound

HRID 2371182Notes

Reaction equation

HRID 2371182 reaction equation
CS(O[CH2:6][C@@H:7]1[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)(=O)=O.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:28]([O:35][C:36]([N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(#N)CCC.CCCC(C)C.C(OCC)(=O)C.O>[CH2:28]([O:35][C:36]([N:38]1[CH2:43][CH2:42][N:41]([CH2:6][C@@H:7]2[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:8]2)[CH2:40][CH2:39]1)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

9

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 643495Benzyl piperazine-1-carboxylateHCID 57686771HCID 57686771, compound

Product 1

HCID 57656859HCID 57656859, compoundYield 70%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 78922-MethylpentaneSolventHCID 8008ButyronitrileSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

tert-Butyl (2R)-2-{[(methylsulfonyl)oxy]methyl}morpholine-4-carboxylate (75 g, 0.25 mol), sodium iodide (11.4 g, 76 mmol), potassium carbonate (38 g, 0.28 mol) and benzyl-1-piperazine carboxylate (54 mL, 0.28 mol) were heated together in butyronitrile (1.5 L) at 115° C. for 24 hours. Water (1.8 L) was added and the layers separated, the aqueous phase was washed with ethyl acetate (1 L) and the combined organics were washed with brine (1 L), dried (MgSO4) and evaporated to give crude product as a yellow oil. Chromatography (5 kg column: 20% ethyl acetate to 50% ethyl acetate in isohexane) gave product as pale yellow gum (73 g, 0.17 mol, 70%).

Workup

  1. customthe layers separated
  2. washthe aqueous phase was washed with ethyl acetate (1 L)
  3. washthe combined organics were washed with brine (1 L)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give crude product as a yellow oil

Sources & evidence

ORD record
ord-6fd6d579db264abf990a149e90b3a63f
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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