Methane → Tert-butyl cyclopropyl(3-(3-methoxypropyl)-5-methylbenzyl)carbamate

HRID 337636Notes

Reaction equation

HRID 337636 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]=[C:15]([CH:24]=O)[CH:14]=2)[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:14]=[C:15]([CH3:24])[CH:16]=[C:17]([CH2:19][CH2:20][CH2:21][O:22][CH3:23])[CH:18]=2)[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 86651678tert-Butyl cyclopropyl{3-formyl-5-[(1E)-3-methoxy-1-propen-1-yl]benzyl}carbamate

Product 1

HCID 86651679Tert-butyl cyclopropyl(3-(3-methoxypropyl)-5-methylbenzyl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl cyclopropyl{3-formyl-5-[(1E)-3-methoxy-1-propen-1-yl]benzyl}carbamate (1 eq.) from the previous step and 10% w/w palladium over charcoal (0.1 eq.) were suspended in EtOAc (0.1 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-787d61e977d94025a2fff4ba35496566
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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