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

HRID 523987

반응식

HRID 523987 반응식
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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 887Methanol용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1979cb4f0c68403c9e15e365b6562dbe
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340510B2

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