Ethanol → (S)-2-(Trifluoromethyl)-3-(benzylamino)propane-1,2-diol

HRID 886707Notes

Reaction equation

HRID 886707 reaction equation
C([O:6][CH2:7][C@@:8]([OH:22])([CH2:13][NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]([F:12])([F:11])[F:10])(=O)CCC.C(O)C>Cl>[F:10][C:9]([F:11])([F:12])[C@@:8]([CH2:13][NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([OH:22])[CH2:7][OH:6]

Participants

4

Reactant 2

HCID 702EthanolHCID 59487502Butanoic acid (S)-2-hydroxy-2-(trifluoromethyl)-3-(benzylamino)propyl ester

Product 1

HCID 59487491(S)-2-(Trifluoromethyl)-3-(benzylamino)propane-1,2-diolYield 104.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(S)-3,3,3-Trifluoro-2-hydroxy-2-{[(phenylmethyl)amino]methyl}propyl butanoate (0.32 g) was dissolved in 5M hydrochloric acid (5 ml) and ethanol (5 ml) and heated at 100° C. for 3 hours. After cooling, the ethanol was evaporated and the remaining aqueous was basified with 2M sodium hydroxide and extracted with ethyl acetate (2 times). The combined organics were dried using a hydrophobic frit and evaporated to give the title compound as a pale yellow oil (0.26 g).

Workup

  1. temperatureAfter cooling
  2. customthe ethanol was evaporated
  3. extractionextracted with ethyl acetate (2 times)
  4. customThe combined organics were dried
  5. customevaporated

Sources & evidence

ORD record
ord-ca916cdd642b4f43a25789870b31a6e0
Source dataset
uspto-grants-2012_08
Patent number
US08247377B2

Reaction notes

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