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

HRID 1931538ノート

反応式

HRID 1931538 の反応式
[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

参加物

5

反応物 3

HCID 14502MethylenecyclohexaneHCID 31388TosylchloramideHCID 17977687Phenyltrimethylammonium bromide dibromide

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a stirred suspension of dried Chloramine-T (5.10 g, 20.76 mmol) in CH3CN (100 mL) under a nitrogen atmosphere was added methylenecyclohexane (9.98 g, 104 mmol). 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).

後処理

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

出典と根拠

ORDレコード
ord-9c44492437af4361b191a1631d1af851
出典データセット
uspto-grants-2012_05
特許番号
US08188085B2

反応ノート

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