Iodobenzene → HCID 57459621, compound

HRID 1428504Notes

Reaction equation

HRID 1428504 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C:12]2([CH2:14][CH2:13]2)[NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:15][C:12]2([CH2:13][CH2:14]2)[N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11575IodobenzeneHCID 46942212tert-Butyl 4,7-diazaspiro[2.5]octane-7-carboxylate2×

Product 1

HCID 57459621HCID 57459621, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A stirred solution of 4,7-diaza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester (0.1 g, 0.471 mmol) [C.A.S. 886766-28-5], iodobenzene (0.026 ml, 0.236) and CsOH (0.079 g, 0.471 mmol) in DMSO (1 ml) was heated in a sealed tube at 120° C. for 20 min. After cooling, additional 4,7-diaza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester (2 eq.) was added, and the mixture was then heated at 120° C. for 20 min. The mixture was cooled. The mixture was washed with NH4Cl (aqueous sat. solution) was added and extracted with Et2O. The organic phase was separated, washed with water, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by manifold (Sep-Pak® silica cartridge; DCM as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate D61 (0.021 g, 31%) as a white solid.

Workup

  1. temperatureAfter cooling
  2. temperatureThe mixture was cooled
  3. washThe mixture was washed with NH4Cl (aqueous sat. solution)
  4. additionwas added
  5. extractionextracted with Et2O
  6. customThe organic phase was separated
  7. washwashed with water
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by manifold (Sep-Pak® silica cartridge; DCM as eluent)
  11. customThe desired fractions were collected
  12. concentrationconcentrated in vacuo
  13. customto yield intermediate D61 (0.021 g, 31%) as a white solid

Sources & evidence

ORD record
ord-56289854288d40d1ac66a712e4eaa1e6
Source dataset
uspto-grants-2015_01
Patent number
US08937060B2

Reaction notes

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