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Benzylamine → 1,1,1-Trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-{[(phenylmethyl)amino]methyl}-2-pentanol

HRID 418776
Notes
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Reaction equation

HRID 418776 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:11]=[CH:12][C:13]([O:27][CH3:28])=[C:14]([C:16]([CH3:26])([CH3:25])[CH2:17][C:18]2([C:21]([F:24])([F:23])[F:22])[CH2:20][O:19]2)[CH:15]=1>C(O)C>[F:24][C:21]([F:22])([F:23])[C:18]([CH2:20][NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([OH:19])[CH2:17][C:16]([C:14]1[CH:15]=[C:10]([F:9])[CH:11]=[CH:12][C:13]=1[O:27][CH3:28])([CH3:26])[CH3:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 160992392-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

Product 1

HCID 576159391,1,1-Trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-{[(phenylmethyl)amino]methyl}-2-pentanolYield 95.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Benzylamine (38.6 mL, 0.353 mol) was added in one portion to a stirred solution of racemic 2-{2-[5-fluoro-2-(methyloxy)phenyl]-2-methylpropyl}-2-(trifluoromethyl)oxirane (which may be prepared according to WO 04/063163, 50 g, 0.171 mol) in ethanol (500 mL) at 20° C. and the resulting mixture heated at 80° C. overnight. The solvent was removed under reduced pressure and the resulting oil was purified by silica gel column chromatography eluting with 4% ethyl acetate in cyclohexane to give the title compound as a white solid (65.1 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting oil was purified by silica gel column chromatography
  3. washeluting with 4% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-63051f34dd594a2cbb12d078127ba433
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08093281B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes