Hydrochloric Acid → 5,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-3-(piperidine-1-carbonyl)-5H-furan-2-one

HRID 1940148노트

반응식

HRID 1940148 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Al](C)C.C([O:13][C:14]([C:16]1[C:17](=[O:33])[O:18][C:19]([CH3:32])([CH3:31])[C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1)=O)C.Cl>C(Cl)Cl>[CH3:31][C:19]1([CH3:32])[O:18][C:17](=[O:33])[C:16]([C:14]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:13])=[C:20]1[C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 16682925TrimethylaluminumHCID 544790785,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-2-oxo-2,5-dihydrofuran-3-carboxylic acid ethyl ester

생성물 1

HCID 219484885,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-3-(piperidine-1-carbonyl)-5H-furan-2-one수율 50.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a room temperature solution of piperidine (284 mg, 3.33 mmol) in CH2Cl2 (5 mL) was added trimethylaluminum (2M in hexane, 1.7 mL, 3.4 mmol). After 15 min, the product from Step 1 (310 mg, 0.92 mmol) was added in one portion and the mixture was heated to reflux for 20 h. The resulting solution was cooled and poured into 1M HCl (gas evolution). The organic layer was washed with brine, filtered through cotton and evaporated. Purification by flash chromatography (80% EtOAc/Hex) provided 175 mg of the title compound.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 20 h
  3. temperatureThe resulting solution was cooled
  4. washThe organic layer was washed with brine
  5. filtrationfiltered through cotton
  6. customevaporated
  7. customPurification by flash chromatography (80% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-fc60a16c4c5f4e8d8d719a4ee73be3f7
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05698584

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