Ytterbium triflate → (2R)-3-[[[3-(1,1,2,2-tetrafluoroethoxy) phenyl]methyl][3-[[3-(trifluoro-methyl)phenyl]-methoxy]phenyl]amino]-1,1,1-trifluoro-2-propanol

HRID 1839477Notes

Reaction equation

HRID 1839477 reaction equation
[F:1][C:2]([F:22])([O:6][C:7]1[CH:8]=[C:9]([CH2:13][NH:14][C:15]2[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=2)[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4].[F:23][C:24]([F:30])([F:29])S([O-])(=O)=O.[Yb+3].[F:32][C:33]([F:39])([F:38])S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>C(#N)C.O.C(OCC)C>[F:1][C:2]([F:22])([O:6][C:7]1[CH:8]=[C:9]([CH2:13][N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:13][C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([C:33]([F:39])([F:38])[F:32])[CH:8]=3)[CH:16]=2)[CH2:3][C@@H:2]([OH:6])[C:24]([F:30])([F:29])[F:23])[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:4])[F:5]

Participants

6

Reactant 2

HCID 2733225Ytterbium triflateHCID 109580163-[[[3-(1,1,2,2-Tetrafluoroethoxy)phenyl]methyl]amino]phenol

Product 1

HCID 10167240(2R)-3-[[[3-(1,1,2,2-tetrafluoroethoxy) phenyl]methyl][3-[[3-(trifluoro-methyl)phenyl]-methoxy]phenyl]amino]-1,1,1-trifluoro-2-propanolYield 597.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

EX-20B) A solution of 3-[[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]phenol (5.1 g, 16.2 mmol) from EX-20A, R-(+)-1,1,1-trifluoro-2,3-epoxypropane (1.5 mL, 17.4 mmol), and ytterbium trifluoromethanesulfonate (1.0 g, 10 mol %) in 10 mL of acetonitrile was heated at 50° C. in a sealed glass tube for 4 h. The reaction mixture was cooled to room temperature, then diluted with water and diethyl ether and extracted. The ether layer was washed with saturated aqueous sodium bicarbonate and brine, dried over MgSO4, and concentrated in vacuo to give 5.64 g (81%) of the desired (2R)-3-[[[3-(1,1,2,2-tetrafluoroethoxy]phenyl]methyl][3,3,3-trifluoro-2-hydroxy-propyl)amino]-phenol product as a yellow oil. 1H NMR (acetone-d6) δ 7.41 (t, 1H), 7.23 (d, 1H), 7.16-7.20 (m, 2H), 6.97 (t, 1H), 6.42 (tt, 1H), 6.18-6.24 (m, 3H), 4.77 (s, 2H), 4.43-4.48 (m, 1H), 3.58 (dd, 1H), 3.39 (dd, 1H).

Workup

  1. extractionextracted
  2. washThe ether layer was washed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a38be845197748aa958e6b4ed82b5f3a
Source dataset
uspto-grants-2004_01
Patent number
US06677341B2

Reaction notes

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