Borane;tetrahydrofuran → 3-Amino-3-(3-trifluoromethyl-phenyl)-propan-1-ol

HRID 220667Notes

Reaction equation

HRID 220667 reaction equation
B.O1CCCC1.[NH2:7][CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)[CH2:9][C:10](O)=[O:11]>>[NH2:7][CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=1)[CH2:9][CH2:10][OH:11]

Participants

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 27830533-amino-3-[3-(trifluoromethyl)phenyl]propanoic acid

Product 1

HCID 27662143-Amino-3-(3-trifluoromethyl-phenyl)-propan-1-ol

Procedure

With ice cooling and under argon, 10.9 ml (10.94 mmol) of borane-tetrahydrofuran complex (1M in THF) were introduced. Then 850 mg (3.65 mmol) of 3-amino-3-[3-(trifluoromethyl)phenyl]propanoic acid were added. After 5 minutes, the cooling bath was removed and the mixture was stirred at RT overnight and for 4 h at reflux. After cooling to RT, pieces of ice were added until the evolution of gas came to an end. The mixture was rendered alkaline with 1M aqueous sodium hydroxide solution, diluted with water to a volume of approximately 150 ml, and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulphate, filtered and freed from the solvent on a rotary evaporator. Drying in an HV gave 744 mg (85% of theory) of the title compound in 92% purity.

Workup

  1. customthe cooling bath was removed
  2. temperatureat reflux
  3. temperatureAfter cooling to RT
  4. additionpieces of ice were added until the evolution of gas
  5. additiondiluted with water to a volume of approximately 150 ml
  6. extractionextracted three times with dichloromethane
  7. dry with materialThe combined organic phases were dried over sodium sulphate
  8. filtrationfiltered
  9. customfreed from the solvent on a rotary evaporator
  10. customDrying in an HV

Sources & evidence

ORD record
ord-925f3f73855946de83af15ec7d2103ad
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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