3-(4-Phenylphenoxy)-2-hydroxypropylazide → 1-Amino-3-(biphenyl-4-yloxy)propan-2-ol

HRID 2294347Notes

Reaction equation

HRID 2294347 reaction equation
[H][H].[C:3]1([C:9]2[CH:22]=[CH:21][C:12]([O:13][CH2:14][CH:15]([OH:20])[CH2:16][N:17]=[N+]=[N-])=[CH:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>[Pd].C(O)C>[C:3]1([C:9]2[CH:22]=[CH:21][C:12]([O:13][CH2:14][CH:15]([OH:20])[CH2:16][NH2:17])=[CH:11][CH:10]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 214747683-(4-Phenylphenoxy)-2-hydroxypropylazideHCID 178418361HCID 178418361, compound

Product 1

HCID 166423901-Amino-3-(biphenyl-4-yloxy)propan-2-olYield 106.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrogen was introduced into a mixture of 2.94 g of 3-(4-phenylphenoxy)-2-hydroxypropylazide (prepared as described in Preparation 83), 0.3 g of 10% w/w palladium-on-carbon and 60 ml of ethanol for 3 hours. At the end of this time, insolubles were removed by filtration, and the filtrate was concentrated by evaporation under reduced pressure, to give 2.84 g of the title compound, melting at 137.7° to 146.8° C.

Workup

  1. customAt the end of this time, insolubles were removed by filtration
  2. concentrationthe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-518e6ce62b674bc7b42310cb778c3193
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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