3-[2-(4-Chlorophenoxy)phenyl]-4-hydroxy-1-methylpyrrolidine-2-one → cis-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz-[2,3:6,7]oxepino[4,5-c]pyrrol-1-one

HRID 2040933노트

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HRID 2040933 반응식
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]2[CH:17](O)[CH2:16][N:15]([CH3:19])[C:14]2=[O:20])=[CH:4][CH:3]=1>ClCCl>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C@@H:13]3[C:14](=[O:20])[N:15]([CH3:19])[CH2:16][C@@H:17]3[C:4]=2[CH:3]=1

참가 물질

3

반응물 1

HCID 679797313-[2-(4-Chlorophenoxy)phenyl]-4-hydroxy-1-methylpyrrolidine-2-one

생성물 1

HCID 56960600cis-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz-[2,3:6,7]oxepino[4,5-c]pyrrol-1-one수율 17.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
110 °C

실험 절차

A mixture of 3 g (9.4 mmol) of 3-[2-(4-chlorophenoxy)phenyl]-4-hydroxy-1-methylpyrrolidine-2-one (compound XIIIb) and 40 g of polyphosphoric acid was stirred overnight at 110° C. After cooling down to room temperature, the resulting mixture was poured into 150 mL of an ice-water mixture. 100 mL of dichloromethane were added, and the organic phase was extracted. The aqueous phase was washed with 50 mL of dichloromethane. The organic phases were combined, washed with brine, and evaporated under vacuum. The crude product was purified by column chromatography to obtain 0.5 g of cis-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (compound cis-VIb). Yield: 17.7%.

후처리

  1. temperatureAfter cooling down to room temperature
  2. extractionthe organic phase was extracted
  3. washThe aqueous phase was washed with 50 mL of dichloromethane
  4. washwashed with brine
  5. customevaporated under vacuum
  6. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-3a05f1c2840f4af4a9c91fc97f2207ac
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580972B2

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