Ethyl formate → 7-(3-Bromophenyl)-2-(hydroxymethylene)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one

HRID 2061614ノート

反応式

HRID 2061614 の反応式
[CH3:1][CH2:2][O-:3].[Na+].[Br:5][C:6]1[CH:7]=[C:8]([CH:12]2[CH2:19][CH:18]3[N:20]([S:21]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)(=[O:23])=[O:22])[CH:14](C[C:16](=[O:34])[CH2:17]3)[CH2:13]2)[CH:9]=[CH:10][CH:11]=1.C(OCC)=O>C1COCC1.[NH4+].[Cl-]>[Br:5][C:6]1[CH:7]=[C:8]([CH:12]2[CH2:13][CH:14]3[N:20]([S:21]([C:24]4[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:28][CH:29]=4)(=[O:23])=[O:22])[CH:18]([CH2:17][C:16](=[O:34])[C:1]3=[CH:2][OH:3])[CH2:19]2)[CH:9]=[CH:10][CH:11]=1

参加物

6

反応物 3

HCID 8025Ethyl formateHCID 2723922Sodium ethoxideHCID 673032167-(3-Bromophenyl)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one

生成物 1

HCID 673031627-(3-Bromophenyl)-2-(hydroxymethylene)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒

実験手順

21% NaOEt (6 ml, 16.1 mmol) was added to a solution of 7-(3-Bromophenyl)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one (90) (2.28 g, 4.54 mmol) and ethyl formate (6 ml, 74.5 mmol) in THF (20 ml). The solution was placed into a preheated oil bath at 60° C. After stirring for 30 min, the solution was cooled to ambient temperature, diluted with saturated aqueous NH4Cl, and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered, and concentrated to afford 7-(3-bromophenyl)-2-(hydroxymethylene)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one. Hydrazine monohydrate (3 ml) was added to a solution of 7-(3-bromophenyl)-2-(hydroxymethylene)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one and glacial acetic acid (1 ml) in EtOH (20 ml). After stirring for 18 h, the solution was concentrated to afford compound 92.

後処理

  1. customThe solution was placed into a preheated oil bath at 60° C
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-af228f87e7af4796ab62ba7b5be9323f
出典データセット
uspto-grants-2012_10
特許番号
US08283358B2

反応ノート

読み込み中…