Methanol → (S)-4-([1,4]oxazepan-6-yl)benzonitrile

HRID 515466ノート

反応式

HRID 515466 の反応式
C1([C@H]([N:9]2[CH2:15][C@H:14]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[CH2:13][O:12][CH2:11][CH2:10]2)C)C=CC=CC=1.ClC(OC(Cl)C)=O.CO>ClCCCl>[O:12]1[CH2:13][C@@H:14]([C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[CH2:15][NH:9][CH2:10][CH2:11]1

参加物

5

反応物 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 67283020(S)-4-(4-((R)-1-phenylethyl)-[1,4]oxazepan-6-yl)benzonitrile

生成物 1

HCID 67281424(S)-4-([1,4]oxazepan-6-yl)benzonitrile収率 71.4%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a solution of (S)-4-(4-((R)-1-phenylethyl)-[1,4]oxazepan-6-yl)benzonitrile (0.662 g, 2.16 mmol) in 1,2-dichloroethane (3.60 ml) was added 1-chloroethyl chloroformate (0.772 g, 5.40 mmol) at room temperature. The mixture was refluxed for 8 hours. Methanol (15 ml) was added to the mixture cooled to room temperature. The mixture was refluxed again for 2 hours. The mixture was concentrated in vacuo. The residue was partitioned between aqueous sodium hydrogen carbonate and chloroform. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=96/4) to afford (S)-4-([1,4]oxazepan-6-yl)benzonitrile as pale yellow solid (312 mg, 70%).

後処理

  1. temperatureThe mixture was refluxed for 8 hours
  2. temperatureThe mixture was refluxed again for 2 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe residue was partitioned between aqueous sodium hydrogen carbonate and chloroform
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=96/4)

出典と根拠

ORDレコード
ord-11a78b63f71d4cea9be8990abc8f54c6
出典データセット
uspto-grants-2015_08
特許番号
US09108957B2

反応ノート

読み込み中…