Acetonitrile → 3-[(3-Phenoxyphenyl)[[3-(tetrahydro-2-furanyl)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol

HRID 1017011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1017011
CC#N.[O:4]([C:11]1[CH:12]=[C:13]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]3[CH2:29][CH2:28][CH2:27][O:26]3)[CH:20]=2)[CH:14]=[CH:15][CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[F:30][C:31]([F:36])([F:35])[CH:32]1[O:34][CH2:33]1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3]>C(OCC)C.CCO>[O:4]([C:11]1[CH:12]=[C:13]([N:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]3[CH2:29][CH2:28][CH2:27][O:26]3)[CH:20]=2)[CH2:33][CH:32]([OH:34])[C:31]([F:36])([F:35])[F:30])[CH:14]=[CH:15][CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

7

Edukt 4

HCID 6342AcetonitrileHCID 5207692-(Trifluoromethyl)oxiraneHCID 2733225Ytterbium triflateHCID 23506095N-(3-phenoxyphenyl)-[[3-(tetrahydro-2-furanyl)phenyl]methyl]amine

Produkt 1

HCID 235060483-[(3-Phenoxyphenyl)[[3-(tetrahydro-2-furanyl)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanolAusbeute 30,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a CH3CN (1 mL) solution of the amine (0.32 g, 0.93 mmol) from EX-608E was added 1.1,1-trifluoro-2,3-epoxypropane (0.24 mL, 2.8 mmol) and Yb(OTf)3 (0.115 g, 0.18 mmol). The cloudy solution was stirred in a sealed flask at 40° C. for 18 h. The cooled reaction mixture was diluted with diethyl ether and washed with water and brine. The organic layer was dried (MgSO4) and evaporated to an oil. Purification by flash chromatography on silica gel eluting with 15% ethyl acetate in hexane gave an oil which was dissolved in EtOH, stripped and dried in vacuo to give 0.13 g (30%) of the desired 3-[(3-phenoxyphenyl)[[3-(tetrahydro-2-furanyl)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol product as a colorless oil. Anal. calcd. for C26H26NO3F3.0.5 EtOH: C, 67.33; H, 6.04; N, 2.94.Found: C, 67.49; H, 6.08; N, 2.91.HRMS calcd. 458.1943 [M+H]+, found: 458.1937. 1H NMR (C6D6) δ0.45 (d, 1H), 1.43 (m, 3H), 1.79 (m, 1H), 1.99 (m, 1H), 3.24 (m, 1H), 3.43 (m, 1H), 3.76 (m, 2H), 4.24 (s, 2H), 4.60 (t, 1H), 6.35 (m, 1H), 6.43 (dd, 1H), 6.54 (dd, 1H), 6.8 (m, 2H), 6.9-7.0 (m, 7H), 7.15 (d, 1H).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated to an oil
  5. customPurification by flash chromatography on silica gel eluting with 15% ethyl acetate in hexane
  6. customgave an oil which
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b4d36698358743ca953e7c51998adf04
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06476057B1

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