{5-[(1R)-2-[Bis(phenylmethyl)amino]-1-hydroxyethyl]-2-[({[2-(trimethylsilyl)ethyl]oxy}methyl)oxy]phenyl}formamide → {5-[(1R)-2-Amino-1-hydroxyethyl]-2-[({[2-(trimethylsilyl)ethyl]oxy}methyl)oxy]phenyl}formamide

HRID 494169Notes

Reaction equation

HRID 494169 reaction equation
C1(C[N:8](CC2C=CC=CC=2)[CH2:9][C@@H:10]([C:12]2[CH:13]=[CH:14][C:15]([O:21][CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=[C:16]([NH:18][CH:19]=[O:20])[CH:17]=2)[OH:11])C=CC=CC=1.[H][H]>CCOC(C)=O.CCO.[Pd].[OH-].[OH-].[Pd+2]>[NH2:8][CH2:9][C@@H:10]([C:12]1[CH:13]=[CH:14][C:15]([O:21][CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=[C:16]([NH:18][CH:19]=[O:20])[CH:17]=1)[OH:11]

Participants

7

Reactant 2

HCID 86606168{5-[(1R)-2-[Bis(phenylmethyl)amino]-1-hydroxyethyl]-2-[({[2-(trimethylsilyl)ethyl]oxy}methyl)oxy]phenyl}formamideHCID 178418361HCID 178418361, compound

Product 1

HCID 86606169{5-[(1R)-2-Amino-1-hydroxyethyl]-2-[({[2-(trimethylsilyl)ethyl]oxy}methyl)oxy]phenyl}formamideYield 89.7%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of {5[(1R)-2-[bis(phenylmethyl)amino]-1-hydroxyethyl}-2-[({[2-(trimethylsilyl)ethyl]oxy}methyl)oxy]phenyl}formamide (90 mg) in EtOAc (8 ml) and EtOH (8 ml) was hydrogenated over 10% palladium on carbon (40 mg) and 20% palladium hydroxide on carbon (20 mg). When hydrogen uptake had ceased the mixture was filtered through celite and the solvent evaporated in vacuo to give the title compound (52 mg). LCMS RT=2.31 min.

Workup

  1. filtrationwas filtered through celite
  2. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-61e6e6ca47a4414b8b2ebca4ad2b4ef5
Source dataset
uspto-grants-2009_05
Patent number
US07538127B2

Reaction notes

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