Benzylamine → 3-(Benzylamino)-1,1,1-trifluoropropan-2-ol

HRID 1966319Notes

Reaction equation

HRID 1966319 reaction equation
[O-]S(C(F)(F)F)(=O)=O.[Li+].[F:10][C:11]([F:16])([F:15])[CH:12]1[CH2:14][O:13]1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC#N>[CH2:17]([NH:24][CH2:14][CH:12]([OH:13])[C:11]([F:16])([F:15])[F:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 5207692-(Trifluoromethyl)oxiraneHCID 3664839Trifluoromethanesulfonic acid, lithium salt

Product 1

HCID 37877943-(Benzylamino)-1,1,1-trifluoropropan-2-ol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-10 °C

Procedure

Lithium triflate was suspended in CH3CN (15 mL) and the mixture is cooled to −10° C. 2-(Trifluoromethyl)oxirane is added and the suspension is allowed to warm to RT with stirring. Benzylamine (6.33 mL, 58 mmol, Aldrich) is added all-at-once and the resultant solution is stirred for 25 minutes. The reaction is quenched by pouring into CH2Cl2 (200 mL) and washing 3× with H2O (200 mL). The organic layer is dried over Na2SO4 and filtered. The product is purified on a Biotage Flash 75L using 20:70:10 CH2Cl2: pentane: triethylamine as eluent. The product containing fractions are pooled and the solvent is removed by rotary evaporation. The product is dried under vacuum at 100° C. yielding a white crystalline solid.

Workup

  1. temperatureto warm to RT
  2. stirringis stirred for 25 minutes
  3. customThe reaction is quenched
  4. additionby pouring into CH2Cl2 (200 mL)
  5. washwashing 3× with H2O (200 mL)
  6. dry with materialThe organic layer is dried over Na2SO4
  7. filtrationfiltered
  8. customThe product is purified on a Biotage Flash 75L
  9. additionThe product containing fractions
  10. customthe solvent is removed by rotary evaporation
  11. customThe product is dried under vacuum at 100° C.
  12. customyielding a white crystalline solid

Sources & evidence

ORD record
ord-f8cea3afce68461aa3ed3ff4ad81ec87
Source dataset
uspto-grants-2013_04
Patent number
US08420646B2

Reaction notes

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