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

HRID 523987

Reaction equation

HRID 523987 reaction equation
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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-1979cb4f0c68403c9e15e365b6562dbe
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Linked notes

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