HCID 86650250, compound → 2-Amino-2-(3-bromo-phenyl)-propane-1,3-diol

HRID 81523Notes

Reaction equation

HRID 81523 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([N+:13]([O-])=O)([CH2:11][OH:12])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.[H][H]>CCO.[Ni]>[NH2:13][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([CH2:11][OH:12])[CH2:9][OH:10]

Participants

5

Reactant 2

HCID 86650250HCID 86650250, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 666656252-Amino-2-(3-bromo-phenyl)-propane-1,3-diol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(3-bromo-phenyl)-2-nitro-propane-1,3-diol (6.79 g, 24.59 mmol) in 100 ml of EtOH was hydrogenated in the presence of 5 g of Raney-Ni. When the take-up of hydrogen had ceased, the mixture was filtered through Celite, and the filtrate was chromatographed on silica gel (EtOAc/MeOH/25% aqueous NH3, 5%) to give the title compound in the form of a colourless solid. TLC (EtOAc/MeOH/25% aqueous NH3, 5%): Rf=0.24; HPLC: RtH2=2.354 min; 1H-NMR (400 MHz, CD3OD): 7.73 (s, 1H), 7.50 (d, 1H), 7.44 (d, 1H), 7.29 (t, 1H), 3.79 (d, 2H), 3.72 (d, 2H); MS: 246, 248 [(M+H)+].

Workup

  1. filtrationthe mixture was filtered through Celite
  2. customthe filtrate was chromatographed on silica gel (EtOAc/MeOH/25% aqueous NH3, 5%)

Sources & evidence

ORD record
ord-96a20de862cd422fb589b26f3fc1521f
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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