Methane → HCID 66896218, compound

HRID 337633Notes

Reaction equation

HRID 337633 reaction equation
[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:11][C:12]1[CH:17]=[C:16](/[CH:18]=[CH:19]/[CH2:20][O:21][CH3:22])[CH:15]=[C:14](/[CH:23]=[CH:24]/[CH2:25][O:26][CH3:27])[CH:13]=1)[CH:8]1[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:11][C:12]1[CH:13]=[C:14]([CH2:23][CH2:24][CH2:25][O:26][CH3:27])[CH:15]=[C:16]([CH2:18][CH2:19][CH2:20][O:21][CH3:22])[CH:17]=1)[CH:8]1[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 297MethaneHCID 67062353HCID 67062353, compound

Product 1

HCID 66896218HCID 66896218, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl{3,5-bis[(1E)-3-methoxy-1-propen-1-yl]benzyl}cyclopropylcarbamate (1 eq.) from the previous step and 10% w/w palladium over charcoal (0.1 eq.) were suspended in EtOAc (0.05 M). The vessel was then evacuated and purged with H2. Under a balloon-filled H2 atmosphere, the reaction suspension was stirred at RT for 3 h. The reaction suspension was then quenched with dichloromethane and filtered through a bed of celite. Concentration of the filtrate in vacuo to afford the title compound as a yellow oil.

Workup

  1. customThe vessel was then evacuated
  2. custompurged with H2
  3. customThe reaction suspension was then quenched with dichloromethane
  4. filtrationfiltered through a bed of celite

Sources & evidence

ORD record
ord-83f4329025484956b15314d06d2249f1
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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