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4-Methyl-3-nitro-1,1,1-trifluoro-2-pentanol → 3-Amino-1,1,1-trifluoro-4-methylpentan-2-ol

HRID 1004220
Notes
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Reaction equation

HRID 1004220 reaction equation
[CH3:1][CH:2]([CH3:13])[CH:3]([N+:10]([O-])=O)[CH:4]([OH:9])[C:5]([F:8])([F:7])[F:6].[H][H]>C(O)(C)C.C(O)(=O)C.[Pd]>[NH2:10][CH:3]([CH:2]([CH3:13])[CH3:1])[CH:4]([OH:9])[C:5]([F:6])([F:7])[F:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 187920764-Methyl-3-nitro-1,1,1-trifluoro-2-pentanolHCID 178418361HCID 178418361, compound

Product 1

HCID 145032463-Amino-1,1,1-trifluoro-4-methylpentan-2-ol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 3776
Isopropanol
Solvent

Conditions

Temperature
5 °C

Procedure

A solution of 4-methyl-3-nitro-1,1,1-trifluoro-2-pentanol (17.1 g) in isopropanol (115 ml) and acetic acid (0.43 ml) was hydrogenated over 10% palladium on carbon (2.4 g) at 3.5 bar pressure until uptake of hydrogen was complete. The catalyst was removed by filtration through diatomaceous earth and the filter cake washed with isopropanol. The filtrate was evaporated under vacuum until no further isopropanol distilled and the residue dissolved in acetonitrile (40 ml). A solution of oxalic acid (3.94 g) in acetonitrile (80 ml) was added with stirring and the mixture cooled to 5° C. The product which crystallised was collected by filtration, washed with cold acetonitrile and dried at 50° C. to give 3-amino-4-methyl-1,1,1-trifluoro-2-pentanol as its oxalate salt (9.08 g).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. washthe filter cake washed with isopropanol
  3. customThe filtrate was evaporated under vacuum until no further isopropanol
  4. distillationdistilled
  5. dissolutionthe residue dissolved in acetonitrile (40 ml)
  6. additionA solution of oxalic acid (3.94 g) in acetonitrile (80 ml) was added
  7. customThe product which crystallised
  8. filtrationwas collected by filtration
  9. washwashed with cold acetonitrile
  10. customdried at 50° C.

Sources & evidence

ORD record
ord-d1865a6a4a024d7bafd5b3d55862a951
Source dataset
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06048889

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes