Piconol → 9-((5-Hydroxypentyl)aminomethyl)anthracene

HRID 891185Notes

Reaction equation

HRID 891185 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][NH:16]O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.N1C=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][OH:40]>CO>[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][NH:16][CH2:37][CH2:36][CH2:35][CH2:34][CH2:39][OH:40])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11474PiconolHCID 90495Di-tert-butyl dicarbonateHCID 22244783HCID 22244783, compound

Product 1

HCID 108809079-((5-Hydroxypentyl)aminomethyl)anthracene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The General Procedure for the N-Boc protection of N-(Anthracen-9-ylmethyl)amino alcohols 4 to give 5. The solution of N-(anthracen-9-ylmethyl)-amino alcohol (5 mmol) in 20 mL of pyridine-methanol (1:5 v/v) was stirred at 0° C. for 10 min. A solution of di-tert-butyl dicarbonate (7.5 mmol) in methanol (5 mL) was added dropwise over ten minutes. The temperature was allowed to rise to room temperature and the reaction was stirred overnight. The mixture was evaporated to dryness under reduced pressure. The residue was dissolved in methylene chloride, and washed with deionized water several times. The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel.

Workup

  1. customto rise to room temperature
  2. customThe mixture was evaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed with deionized water several times
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-2f5380f1109a467c8233de729787448b
Source dataset
uspto-grants-2006_02
Patent number
US07001925B1

Reaction notes

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