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 644961Notes

Reaction equation

HRID 644961 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-2900873af7d44aa9a1ee13d90518334d
Source dataset
uspto-grants-2010_04
Patent number
US07700658B2

Reaction notes

Loading…