Ammonium Chloride → Dimethyl 7-(3-bromophenyl)-3-oxo-9-azabicyclo[3.3.1]nonane-2,4-dicarboxylate

HRID 2061611ノート

反応式

HRID 2061611 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:12][CH:13]=O)[CH2:9][CH:10]=O)[CH:5]=[CH:6][CH:7]=1.[O:15]=[C:16]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:17][C:18]([O:20][CH3:21])=[O:19].[Cl-].[NH4+:28].C([O-])(=O)C.[Na+]>C1COCC1.Cl.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:9][CH:10]3[NH:28][CH:13]([CH:17]([C:18]([O:20][CH3:21])=[O:19])[C:16](=[O:15])[CH:22]3[C:23]([O:25][CH3:26])=[O:24])[CH2:12]2)[CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 74591Dimethyl 3-oxoglutarateHCID 517045Sodium AcetateHCID 866405263-(3-Bromophenyl)pentanedial

生成物 1

HCID 70230991Dimethyl 7-(3-bromophenyl)-3-oxo-9-azabicyclo[3.3.1]nonane-2,4-dicarboxylate

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

3-(3-Bromophenyl)pentanedial (87), dimethyl 3-oxopentanedioate (88) (5.78 g, 33.2 mmol), ammonium chloride (14.42 g, 270 mmol) in THF (100 ml), 10% aqueous HCl (100 ml), and water (100 ml) was stirred for 18 h. Sodium acetate was then added until the pH was 4-5. After stirring for 6 h, the solution was extracted with EtOAc. The combined organic extracts were washed with saturated aqueous Na2CO3, dried over MgSO4, filtered and concentrated to afford compound 89.

後処理

  1. extractionthe solution was extracted with EtOAc
  2. washThe combined organic extracts were washed with saturated aqueous Na2CO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-b0a91de798944150bc276bd92cf9470f
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…