Benzylamine → (R)-3-Benzylamino-1,1,1-trifluoro-propan-2-ol

HRID 922771Notes

Reaction equation

HRID 922771 reaction equation
FC(F)(F)S([O-])(=O)=O.[Li+].[F:10][C:11]([F:16])([F:15])[C@@H:12]1[O:14][CH2:13]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][CH2:13][C@@H:12]([OH:14])[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 3664839Trifluoromethanesulfonic acid, lithium saltHCID 7016923(2R)-2-(trifluoromethyl)oxirane

Product 1

HCID 1477381(R)-3-Benzylamino-1,1,1-trifluoro-propan-2-olYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of lithium trifluoromethanesulfonate (1.43 g, 9.17 mmol) in CH3CN (30 ml) was added (R)-(+)-3,3,3-trifluoro-1,2-epoxypropane (10.77 g, 96 mmol) slowly at −10° C. After 5 minutes benzylamine (10 ml, 92 mmol) was added slowly. The mixture was allowed to warm as the bath warmed to rt overnight. The mixture was concentrated. The crude product was subjected to silica gel chromatography (330 g, 0-50% EtOAc/hexanes, 10 minute gradient) to afford (R)-3-(benzylamino)-1,1,1-trifluoropropan-2-ol (4-2, 15.9 g, 79%) as a white solid. LRMS m/z (M+H)+ 220.2 calc. 220.1 found.

Workup

  1. temperatureto warm as the bath
  2. concentrationThe mixture was concentrated
  3. customwas subjected to silica gel chromatography (330 g, 0-50% EtOAc/hexanes, 10 minute gradient)

Sources & evidence

ORD record
ord-5e4e0ea6ec8b47a4ad1e0259f7c41e92
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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