Methylenecyclohexane → 1-[(4-methylphenyl)sulfonyl]-1-Azaspiro[2.5]octane

HRID 1023828

Reaction equation

HRID 1023828 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11]Cl)(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH2:13]=[C:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[Br-].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>CC#N>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[C:14]3([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:13]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14502MethylenecyclohexaneHCID 31388TosylchloramideHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 111497721-[(4-methylphenyl)sulfonyl]-1-Azaspiro[2.5]octaneYield 48.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of dried Chloramine-T (5.10 g, 20.76 mmol) in CH3CN (100 mL) under a nitrogen atmosphere methylenecyclohexane (9.98 g, 104 mmol) was added. Phenyltrimethylammonium tribromide (7.80 g, 20.76 mmol) was added in three portions over 10 min. The mixture was stirred at room temperature for 16 hours. The solvent was evaporated and the residue was partitioned between dichloromethane and water. The organic layer was dried over Na2SO4 and the solvent was evaporated. The residue was chromatographed on silica gel with an ISCO Combiflash using EtOAc/hexanes (5-30% gradient) to afford the title compound as a white solid (2.66 g).

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between dichloromethane and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent was evaporated
  6. customThe residue was chromatographed on silica gel with an ISCO Combiflash

Sources & evidence

ORD record
ord-9d61fe0b5e3049a380a1f5b4ab11c292
Source dataset
uspto-grants-2014_05
Patent number
US08722727B2

Linked notes

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