Benzylamine → (R)-3-Benzylamino-1,1,1-trifluoro-propan-2-ol

HRID 922771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 922771
FC(F)(F)S([O-])(=O)=O.[Li+].[F:10][C:11]([F:16])([F:15])[C@@H:12]1[O:14][CH2:13]1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC#N>[CH2:17]([NH:24][CH2:13][C@@H:12]([OH:14])[C:11]([F:16])([F:15])[F:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 7504BenzylamineHCID 3664839Trifluoromethanesulfonic acid, lithium saltHCID 7016923(2R)-2-(trifluoromethyl)oxirane

Produkt 1

HCID 1477381(R)-3-Benzylamino-1,1,1-trifluoro-propan-2-olAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of lithium trifluoromethanesulfonate (1.43 g, 9.17 mmol) in CH3CN (30 ml) was added (R)-(+)-3,3,3-trifluoro-1,2-epoxypropane (10.77 g, 96 mmol) slowly at −10° C. After 5 minutes benzylamine (10 ml, 92 mmol) was added slowly. The mixture was allowed to warm as the bath warmed to rt overnight. The mixture was concentrated. The crude product was subjected to silica gel chromatography (330 g, 0-50% EtOAc/hexanes, 10 minute gradient) to afford (R)-3-(benzylamino)-1,1,1-trifluoropropan-2-ol (4-2, 15.9 g, 79%) as a white solid. LRMS m/z (M+H)+ 220.2 calc. 220.1 found.

Aufarbeitung

  1. temperatureto warm as the bath
  2. concentrationThe mixture was concentrated
  3. customwas subjected to silica gel chromatography (330 g, 0-50% EtOAc/hexanes, 10 minute gradient)

Quellen und Nachweise

ORD-Eintrag
ord-5e4e0ea6ec8b47a4ad1e0259f7c41e92
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278960B2

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