Methanesulfonyl chloride → 1,2-Dihydro-1'-methyl-1-(methylsulfonyl)-spiro[3H-indole-3,4'-piperidine]

HRID 1586392ノート

反応式

HRID 1586392 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)[CH2:4][CH2:3]1.[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:17]([CH3:16])(=[O:19])=[O:18])[CH2:8]2)[CH2:6][CH2:7]1

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 128015871'-Methylspiro[indoline-3,4'-piperidine]

生成物 1

HCID 212167761,2-Dihydro-1'-methyl-1-(methylsulfonyl)-spiro[3H-indole-3,4'-piperidine]収率 81.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Dissolve 1,2-dihydro-1'-methyl-spiro[3H-indole-3,4'-piperidine] (3.0 g, 14.8 mmoles) in dry CH2Cl2 (25 ml) and cool under N2 in an ice bath. Add, dropwise, methane sulfonyl chloride (1.5 ml, 19.3 mmoles), followed by ethyl diisopropyl amine (5.0 ml, 28.7 mmoles). Warm to room temperature and stir overnight. Dilute the solution to 100 ml with CH2Cl2. Wash the solution with saturated aqueous NaHCO3 (4×25 ml), then with water. Dry solution with anhydrous Na2SO4, then remove the solvent using reduced pressure. Purify the resulting reaction mixture by flash chromatography (SiO2) using 5% MeOH(NH3)/EtOAc as eluent. Yield: 3.37 g (81%) of the title compound.

後処理

  1. temperaturecool under N2 in an ice bath
  2. additionAdd
  3. washWash the solution with saturated aqueous NaHCO3 (4×25 ml)
  4. customDry solution with anhydrous Na2SO4, then remove the solvent
  5. customPurify
  6. customthe resulting reaction mixture by flash chromatography (SiO2)

出典と根拠

ORDレコード
ord-c34f1553a97a4733a75facc5ee41f231
出典データセット
uspto-grants-1999_08
特許番号
US05945428

反応ノート

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