Water → HCID 90052087, compound

HRID 2284664Notes

Reaction equation

HRID 2284664 reaction equation
[F:1][C:2]([F:19])([F:18])[CH:3]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[C:4](OC)=[O:5].[BH4-].[Na+].O.C(OCC)(=O)C>C(O)C>[F:1][C:2]([F:18])([F:19])[CH:3]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 90051730HCID 90051730, compound

Product 1

HCID 90052087HCID 90052087, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 3,3,3-trifluoro-2-((3-nitrophenyl)amino)propanoate (C13, 297 mg) in ethanol (10 mL), sodium borohydride (121 mg) was added at room temperature, and the mixture was stirred at the same temperature for 4 hours. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 50% hexane in ethyl acetate) to obtain 3,3,3-trifluoro-2-((3-nitrophenyl)amino)propan-1-ol (C14, 197 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 50% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-93c7044486c54c408f6ba6669b35803d
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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