2-(Trifluoromethyl)oxirane → 1,1,1-Trifluoro-3-((3-phenoxyphenyl)(3-(2,2,2-trifluoroethoxy)benzyl)amino)propan-2-ol
Reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])[CH:17]=2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:28][C:29]([F:34])([F:33])[CH:30]1[O:32][CH2:31]1>>[O:1]([C:8]1[CH:9]=[C:10]([N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]([F:25])([F:26])[F:27])[CH:17]=2)[CH2:31][CH:30]([OH:32])[C:29]([F:34])([F:33])[F:28])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
The N-(3-phenoxyphenyl)[[3-(2,2,2-trifluoroethoxy)phenyl]methyl]amine (0.50 g, 1.35 mmol) product from EX-659B and 1,1,1-trifluoro-2,3-epoxy-propane (1.0 ml, 11 mmol) were heated to 90° C. in a sealed container under argon for 2 d. The resulting mixture was eluted from silica gel with 4% ethyl acetate in hexane, and fractions were pooled based on TLC analysis to give 134 mg (21%) of the desired 3[(3-phenoxyphenyl)[[3-(2,2,2-trifluoroethoxy)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol product as a clear, colorless oil. 1H NMR (C6D6) δ6.80-7.08 (m, 7H), 6.64 (d, 1H), 6.53 (bt, 1H), 6.49 (t, 1H), 6.44 (dd, 1H), 6.34 (dt, 2H), 4.23 (s, 2H), 3.84 (m, 1H), 3.61 (m, 2H), 3.53 (dd, 1H), 3.20 (m, 1H), 2.03 (d, 1H). 19F NMR (C6D6) δ−74.20 (t, 3F), −78.95 (d, 3F). HRMS calcd. for C24H21F6NO3: 486.1504 [M+H]+, found: 486.1498.
Workup
- washThe resulting mixture was eluted from silica gel with 4% ethyl acetate in hexane, and fractions
Sources & evidence
- ORD record
- ord-80aae0a7d97445c79417733fa6f43fec
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06458852B1
Reaction notes
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