1,1-Dimethylethyl cyclopropyl({2,3-dichloro-5-[(2E)-3-cyano-2-propen-1-yl]phenyl}methyl)carbamate → 1,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(3-cyanopropyl)phenyl]methyl}carbamate

HRID 337561Notes

Reaction equation

HRID 337561 reaction equation
[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17]([CH2:19]/[CH:20]=[CH:21]/[C:22]#[N:23])[CH:16]=[C:15]([Cl:24])[C:14]=2[Cl:25])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17]([CH2:19][CH2:20][CH2:21][C:22]#[N:23])[CH:16]=[C:15]([Cl:24])[C:14]=2[Cl:25])[C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:10])[CH3:8])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 669007271,1-Dimethylethyl cyclopropyl({2,3-dichloro-5-[(2E)-3-cyano-2-propen-1-yl]phenyl}methyl)carbamate

Product 1

HCID 668959521,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(3-cyanopropyl)phenyl]methyl}carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1-dimethylethyl cyclopropyl({2,3-dichloro-5-[(2E)-3-cyano-2-propen-1-yl]phenyl}methyl)carbamate (1 eq.) from the previous step in EtOAc (0.04 M) was added palladium (10% w/w over activated carbon, 0.1 eq). The vessel was evacuated and back filled with hydrogen. The reaction suspension was then stirred under a balloon atmosphere of hydrogen for 1.5 h. The reaction was quenched with dichloromethane and filtered through a bed of celite. The insolubles were washed further with EtOAc. Concentration of the filtrate in vacuo afforded the title compound as a colorless oil.

Workup

  1. customThe vessel was evacuated
  2. additionback filled with hydrogen
  3. customThe reaction was quenched with dichloromethane
  4. filtrationfiltered through a bed of celite
  5. washThe insolubles were washed further with EtOAc

Sources & evidence

ORD record
ord-d0b59d2b5e0a4265b18bdd3a6e779e36
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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