Tert-butyl {2-[3-(benzyloxy)phenyl]ethyl}carbamate → tert-Butyl 3-hydroxyphenethylcarbamate

HRID 1261449Notes

Reaction equation

HRID 1261449 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16]CC2C=CC=CC=2)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59596820Tert-butyl {2-[3-(benzyloxy)phenyl]ethyl}carbamate

Product 1

HCID 11031911tert-Butyl 3-hydroxyphenethylcarbamateYield 101.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1 g of Pd/C 10% was added to a solution of 13 g (0.039 mol) of [2-(3-benzyloxy-phenyl)-ethyl]-carbamic acid tert-butyl ester in 100 ml of ethanol. The mixture was hydrogenated at 40 psi overnight. The catalyst was filtered off and washed with ethanol. The solvent was removed under vacuum and 9.4 g of the title compound were obtained as a colourless oil in quantitative yield.

Workup

  1. customwas hydrogenated at 40 psi overnight
  2. filtrationThe catalyst was filtered off
  3. washwashed with ethanol
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-628217ece8404e0c861b619fde3db365
Source dataset
uspto-grants-2013_06
Patent number
US08470877B2

Reaction notes

Loading…