2-(Trifluoromethyl)-3-(benzylamino)propane-1,2-diol → 1,2-Propanediol, 2-(aminomethyl)-3,3,3-trifluoro-

HRID 886695Notes

Reaction equation

HRID 886695 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([CH2:7][NH:8]CC1C=CC=CC=1)([OH:6])[CH2:4][OH:5]>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:8][CH2:7][C:3]([OH:6])([C:2]([F:17])([F:16])[F:1])[CH2:4][OH:5]

Participants

4

Reactant 1

HCID 248097812-(Trifluoromethyl)-3-(benzylamino)propane-1,2-diol

Product 1

HCID 248097501,2-Propanediol, 2-(aminomethyl)-3,3,3-trifluoro-Yield 95.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 3,3,3-trifluoro-2-{[(phenylmethyl)amino]methyl}-1,2-propanediol (8.33 g, 33.4 mmol) in ethanol (550 ml) containing palladium hydroxide on carbon (20%, 800 mg) was stirred under an atmosphere of hydrogen for 24 hours. The catalyst was filtered off via a pad of celite and the filtrate was concentrated under reduced pressure, toluene was added and the solution evaporated again under reduced pressure to give the title compound (5.06 g) as an oil.

Workup

  1. filtrationThe catalyst was filtered off via a pad of celite
  2. concentrationthe filtrate was concentrated under reduced pressure, toluene
  3. additionwas added
  4. customthe solution evaporated again under reduced pressure

Sources & evidence

ORD record
ord-c42b2b1722744161942cd27dc0535e31
Source dataset
uspto-grants-2012_08
Patent number
US08247377B2

Reaction notes

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