[(R)-1-(4-benzyloxy-2-methoxy-phenyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester → [(R)-2-Hydroxy-1-(4-hydroxy-2-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

HRID 454968Notes

Reaction equation

HRID 454968 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17]CC2C=CC=CC=2)=[CH:13][C:12]=1[O:25][CH3:26])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=1[O:25][CH3:26])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67073951[(R)-1-(4-benzyloxy-2-methoxy-phenyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 67073547[(R)-2-Hydroxy-1-(4-hydroxy-2-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of [(R)-1-(4-benzyloxy-2-methoxy-phenyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester (136 mg, 0.365 mmol) and Pd/C (˜10 mg) in MeOH (4 ml) was stirred under H2 (1 atm) for overnight. The mixture was filtered and the filtrate was concentrated to give the titled compound (100 mg, 100%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-257a1e73ec614bd995b6d582256420b8
Source dataset
uspto-grants-2013_07
Patent number
US08497271B2

Reaction notes

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