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 2040933

反応式

HRID 2040933 の反応式
[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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
110 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-3a05f1c2840f4af4a9c91fc97f2207ac
出典データセット
uspto-grants-2013_11
特許番号
US08580972B2

関連ノート

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