Hydrochloric Acid → (2S)-2-(2,3,4-Trifluoroanilino)propanol

HRID 458188Notes

Reaction equation

HRID 458188 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:16]([F:17])=[C:15]([F:18])[CH:14]=[CH:13][C:5]=1[NH:6][C@@H:7]([CH3:12])[C:8](OC)=[O:9].Cl.C(=O)([O-])O.[Na+]>CC(O)C.CO>[F:3][C:4]1[C:16]([F:17])=[C:15]([F:18])[CH:14]=[CH:13][C:5]=1[NH:6][C@@H:7]([CH3:12])[CH2:8][OH:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 10125210Methyl (2S)-2-(2,3,4-trifluoroanilino)propionate

Product 1

HCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanolYield 84.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent2×

Conditions

Temperature
50 °C

Procedure

Under ice-cooling, sodium borohydride (1.2 g) was dissolved in IPA (50 ml). After adding methanol (5 ml), a solution of the compound (5.0 g) obtained in Example 1 in IPA was dropped thereinto. Then the liquid reaction mixture was heated to 50° C. and stirred for 1 hour. Next, hydrochloric acid (1 mol/l) was added and the mixture was stirred for a while. Then a saturated aqueous solution of sodium hydrogencarbonate was added and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and filtered. After evaporating the solvent, the obtained residue was subjected to silica gel column chromatography to give 3.7 g (84%) of the title compound as an oily substance.

Workup

  1. temperatureUnder ice-cooling
  2. customThen the liquid reaction mixture
  3. stirringthe mixture was stirred for a while
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customAfter evaporating the solvent

Sources & evidence

ORD record
ord-0a9194ccfbdf42a5b9bca0a88b599eb2
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Reaction notes

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