Methane → 1,1-Dimethylethyl cyclopropyl({2-methyl-5-[3-(methyloxy)propyl]phenyl}methyl)carbamate

HRID 337557Notes

Reaction equation

HRID 337557 reaction equation
[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17](/[CH:19]=[CH:20]/[CH2:21][O:22][CH3:23])[CH:16]=[CH:15][C:14]=2[CH3:24])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1.C>CCOC(C)=O.[Pd]>[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17]([CH2:19][CH2:20][CH2:21][O:22][CH3:23])[CH:16]=[CH:15][C:14]=2[CH3:24])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 297MethaneHCID 668969781,1-Dimethylethyl cyclopropyl({2-methyl-5-[(1E)-3-(methyloxy)-1-propen-1-yl]phenyl}methyl)carbamate

Product 1

HCID 668969791,1-Dimethylethyl cyclopropyl({2-methyl-5-[3-(methyloxy)propyl]phenyl}methyl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1,1-Dimethylethyl cyclopropyl({2-methyl-5-[(1E)-3-(methyloxy)-1-propen-1-yl]phenyl}methyl)carbamate (1 eq.) from the previous step and 10% w/w palladium over charcoal (0.1 eq.) were suspended in EtOAc (0.08 M). The vessel was then evacuated and purged with H2. Under a balloon-filled H2 atmosphere, the reaction suspension was stirred at RT for 2 h. The reaction was then quenched with CH2Cl2, filtered through a bed of celite and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customThe vessel was then evacuated
  2. custompurged with H2
  3. customThe reaction was then quenched with CH2Cl2
  4. filtrationfiltered through a bed of celite
  5. concentrationthe filtrate concentrated in vacuo
  6. customPurification of the crude product
  7. customthus obtained by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-419b5bbc58e04d61bd2aa8fed6408846
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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