Sodium hydride → (r)-5,11-Dihydro-5-[1-(4-dimethylaminophenethyl)pyrrolidine-3-yl]dibenzo[b,e][1,4]oxazepine

HRID 1859453ノート

反応式

HRID 1859453 の反応式
[H-].[Na+].[CH:3]1[C:13]2[CH2:12][O:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:18][N:19]([CH3:38])[C:20]1[CH:37]=[CH:36][C:23]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][C@H:28](OS(C)(=O)=O)[CH2:27]2)=[CH:22][CH:21]=1>CCCCCC.CS(C)=O>[CH3:38][N:19]([CH3:18])[C:20]1[CH:21]=[CH:22][C:23]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][C@@H:28]([N:8]3[C:7]4[CH:6]=[CH:5][CH:4]=[CH:3][C:13]=4[CH2:12][O:11][C:10]4[CH:14]=[CH:15][CH:16]=[CH:17][C:9]3=4)[CH2:27]2)=[CH:36][CH:37]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 110847985,11-Dihydrodibenzo[b,e][1,4]oxazepineHCID 86585524(S)-1-(4-dimethylaminophenethyl)-3-methanesulfonyloxy-pyrrolidine

生成物 1

HCID 12018622(r)-5,11-Dihydro-5-[1-(4-dimethylaminophenethyl)pyrrolidine-3-yl]dibenzo[b,e][1,4]oxazepine

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 8058Hexane溶媒

実験手順

60% sodium hydride (160 mg, 4.0 mmol) was washed with hexane under argon atmosphere, and then suspended in dimethyl sulfoxide (12 ml). After stirring at room temperature for 30 minutes, 5,11-dihydrodibenzo[b,e][1,4]oxazepine (790 g, 4.0 mmol) was added to the obtained suspension. They were stirred at room temperature for 60 minutes and then at 50° C. for 60 minutes. A solution of (S)-1-(4-dimethylaminophenethyl)-3-methanesulfonyloxypyrrolidine (378 mg, 1.21 mmol) in dimethyl sulfoxide (7 ml) was added dropwise in the obtained solution, and they were stirred at 50° C. for 3 hours. The reaction liquid was poured into ice/water. After the extraction with ethyl acetate, the organic layer was dried and the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with hexane and ethyl acetate (10:1), then with hexane and ethyl acetate (3:1) and finally with a mixture of the same solvents (1:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (R)-5,11-dihydro-5-[1-(4-dimethylaminophenethyl)pyrrolidine-3-yl]dibenzo[b,e][1,4]oxazepine in the form of a light yellow oil (196 mg, 39%).

後処理

  1. stirringThey were stirred at room temperature for 60 minutes
  2. waitat 50° C. for 60 minutes
  3. stirringwere stirred at 50° C. for 3 hours
  4. customThe reaction liquid
  5. extractionAfter the extraction with ethyl acetate
  6. customthe organic layer was dried
  7. customthe solvent was evaporated under reduced pressure
  8. washThe product was eluted with hexane and ethyl acetate (10:1)
  9. additionwith hexane and ethyl acetate (3:1) and finally with a mixture of the same solvents (1:1)
  10. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-6775aff3255b49509cda06eaa18e1d3f
出典データセット
uspto-grants-2003_03
特許番号
US06528504B2

反応ノート

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