HCID 18184945, compound → HCID 18184998, compound

HRID 1358576Notes

Reaction equation

HRID 1358576 reaction equation
[C:1]12([C:11]3[CH:35]=[CH:34][C:14]([O:15][C:16]4[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[C:18]([N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH3:26])[CH:17]=4)=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>[Pd].CO>[C:1]12([C:11]3[CH:35]=[CH:34][C:14]([O:15][C:16]4[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([N:25]([C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[CH3:26])[CH:17]=4)=[CH:13][CH:12]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

4

Reactant 1

HCID 18184945HCID 18184945, compound

Product 1

HCID 18184998HCID 18184998, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(4-adamantan-1-ylphenoxy)-2-(N-t-butoxycarbonyl-N-methylamino)nitrobenzene (14 g), palladium on carbon (1.50 g, 10%) and methanol (300 ml) was stirred at room temperature under a hydrogen atmosphere for 2 hours and then 50° C. for 2 hours, allowed to stand at room temperature overnight and then stirred at 50° C. for 2 hours. The insoluble material of the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was chromatographed on a silica gel column using hexane:ethyl acetate=3:1 as the eluant to afford the title compound (6.70 g, mp 85-90° C.).

Workup

  1. wait50° C. for 2 hours
  2. waitto stand at room temperature overnight
  3. stirringstirred at 50° C. for 2 hours
  4. filtrationThe insoluble material of the reaction mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-2f56b0dd5d1149c2b2ec8bbbe8987620
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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