3-Nitro-1-phenoxy-butan-2-ol → (2RS,3RS)-3-amino-1-phenoxy-butan-2-ol

HRID 13075Notes

Reaction equation

HRID 13075 reaction equation
[N+:1]([CH:4]([CH3:15])[CH:5]([OH:14])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-])=O>CO.[Pt]=O>[NH2:1][CH:4]([CH3:15])[CH:5]([OH:14])[CH2:6][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 151053083-Nitro-1-phenoxy-butan-2-ol

Product 1

HCID 15105310(2RS,3RS)-3-amino-1-phenoxy-butan-2-olYield 28.2%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

3-Nitro-1-phenoxy-butan-2-ol (1.7 g, 8.0 mmol) in methanol (50 mL) was hydrogenated over platinum oxide (300 mg) at atmospheric pressure overnight. The mixture was filtered through celite and purified by semi-preparative HPLC (XBridge, C18, 5 μm, 19×50 mm, 12 min gradient of 5-20% acetonitrile in (water+2 mL NH3/L). Fractions containing the faster eluting peak were pooled and concentrated to give the subtitle compound (409 mg).

Workup

  1. filtrationThe mixture was filtered through celite
  2. custompurified by semi-preparative HPLC (XBridge, C18, 5 μm, 19×50 mm, 12 min gradient of 5-20% acetonitrile in (water+2 mL NH3/L)
  3. additionFractions containing the
  4. washfaster eluting peak
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bb4aaec49ea24df39faad60ab1ef980d
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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