Sodium Acetate → (S)-Cyclopropanecarboxylic acid [1-(4-formyl-phenyl)-ethyl]-amide

HRID 523987

反応式

HRID 523987 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]([CH:13]2[CH2:15][CH2:14]2)=[O:12])[CH3:9])=[CH:4][CH:3]=1.[C:16]([O-])(=[O:18])C.[Na+]>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH:16]([C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]([CH:13]2[CH2:15][CH2:14]2)=[O:12])[CH3:9])=[CH:4][CH:3]=1)=[O:18]

参加物

6

反応物 2

HCID 517045Sodium AcetateHCID 800360N-[(1S)-1-(4-bromophenyl)ethyl]cyclopropanecarboxamide

生成物 1

HCID 118940157(S)-Cyclopropanecarboxylic acid [1-(4-formyl-phenyl)-ethyl]-amide

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 887Methanol溶媒

反応条件

温度
100 °C

実験手順

To 5.0 g (19 mmol) (S)-cyclopropanecarboxylic acid [1-(4-bromo-phenyl)-ethyl]-amide (WO 2012/01107) in 40 mL MeOH are added 125 mg (0.600 mmol) palladium-(II)-acetate, 620 mg (1.10 mmol) 1,1′-bis(diphenylphosphino)-ferrocene and 4.6 g (56 mmol) sodium acetate. The mixture is stirred at 100° C. and 5 bar CO atmosphere over night. After that time, the mixture is filtered over celite and the filtrate is concentrated by evaporation. The residue is purified by column chromatography (silica gel; gradient hexane/EtOAc 1:0→1:4) to yield the desired product.

後処理

  1. wait5 bar CO atmosphere over night
  2. filtrationAfter that time, the mixture is filtered over celite
  3. concentrationthe filtrate is concentrated by evaporation
  4. customThe residue is purified by column chromatography (silica gel; gradient hexane/EtOAc 1:0→1:4)

出典と根拠

ORDレコード
ord-1979cb4f0c68403c9e15e365b6562dbe
出典データセット
uspto-grants-2016_05
特許番号
US09340510B2

関連ノート

読み込み中…