Methanol → 2-Amino-2-(4-fluorophenyl)propane-1,3-diol

HRID 2189883Notes

Reaction equation

HRID 2189883 reaction equation
FC1C(NC2C=C(OC(C)C)NN=2)=NC([NH:10][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:12][OH:13])=C(C=1)C#N.[CH3:31][OH:32]>[Ni]>[NH2:10][C:11]([C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)([CH2:12][OH:13])[CH2:31][OH:32]

Participants

4

Reactant 2

HCID 887MethanolHCID 178458666HCID 178458666, compound

Product 1

HCID 674555812-Amino-2-(4-fluorophenyl)propane-1,3-diolYield 61%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A suspension of 2-(4-fluorophenyl)-2-nitroproane-1,3-diol (Method 11; 4.5 g, 20.9 mmol) and Raney nickel (0.45 g, 5.23 mmol) in MeOH (50 ml) was degassed and stirred under H2 (48 psi) for 2 hours. The catalyst was removed by filtration. The filtrate was concentrated and recrystallized from hexane:EtOAc (1:1) to give the title compound (2.35 g, 61%) as a white solid. NMR (400 MHz) 7.55 (m, 2H), 7.07 (m, 2H), 4.65 (t, J=5.2 Hz, 2H), 3.49 (m, 4H), 1.76 (s, 2H).

Workup

  1. customwas degassed
  2. customThe catalyst was removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customrecrystallized from hexane:EtOAc (1:1)

Sources & evidence

ORD record
ord-2b128be45ff44eff888b9e856804f2d1
Source dataset
uspto-grants-2012_12
Patent number
US08324252B2

Reaction notes

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