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

HRID 1925515Notes

Reaction equation

HRID 1925515 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

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

Product 1

HCID 11031911tert-Butyl 3-hydroxyphenethylcarbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of Intermediate 54 (1.4 g, 4.37 mmol) in methanol (50 mL) was added palladium on charcoal (10%, 0.143 g). The reaction mixture was hydrogenated under a balloon pressure at room temperature overnight. The catalyst was filtered through Celite® and the solvent removed under reduced pressure to give the title compound as a solid, which was used in the next step without further purification. MS (M+): 238.

Workup

  1. filtrationThe catalyst was filtered through Celite®
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7b73def1ace345c6815db34634008d02
Source dataset
uspto-grants-2012_05
Patent number
US08178679B2

Reaction notes

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