{4-[4-(2-tert-Butoxycarbonylaminoethoxy)phenyl]butyl}carbamic acid benzyl ester → {2-[4-(4-Aminobutyl)phenoxy]ethyl}carbamic acid tert-butyl ester

HRID 217929Notes

Reaction equation

HRID 217929 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:17][CH:16]=1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[C:28]([O:27][C:25](=[O:26])[NH:24][CH2:23][CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][CH2:12][CH2:11][NH2:10])=[CH:16][CH:17]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

5

Reactant 2

HCID 67364654{4-[4-(2-tert-Butoxycarbonylaminoethoxy)phenyl]butyl}carbamic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 22566154{2-[4-(4-Aminobutyl)phenoxy]ethyl}carbamic acid tert-butyl esterYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

{4-[4-(2-tert-Butoxycarbonylaminoethoxy)phenyl]butyl}carbamic acid benzyl ester 1 (2.5 g, 5.60 mmol), ethanol (20 mL), and 10% palladium on carbon (1 g), were subject to one atmosphere of hydrogen for 4 h, and then allowed to stand overnight. After stirring under nitrogen purge, the catalyst was removed by filtering the reaction mixture through Celite and rinsing with methylene chloride. Evaporation followed by 2 h under high vacuum afforded the product (1.7 g, 98%) as an oil. 1H NMR (300 MHz, CDCl3) δ 1.45 (s, 9H), 1.47 (m, 2H), 1.61 (m, 2H), 1.75 (br s, 2H), 2.56 (t, 2H), 2.71 (t, 2H), 3.51 (m, 2H), 3.99 (t, 2H), 5.07 (br s, 1H), 6.80 (d, 2H), 7.08 (d, 2H).

Workup

  1. custompurge
  2. customthe catalyst was removed
  3. filtrationby filtering the reaction mixture through Celite
  4. washrinsing with methylene chloride
  5. customEvaporation
  6. waitfollowed by 2 h under high vacuum

Sources & evidence

ORD record
ord-413049b4c5b54730b8938f3ec1256761
Source dataset
uspto-grants-2012_06
Patent number
US08198286B2

Reaction notes

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