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

HRID 1586392노트

반응식

HRID 1586392 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c34f1553a97a4733a75facc5ee41f231
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05945428

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