Sodium Sulfate → (S)-2-Amino-6,6,6-trifluoro-5-phenyl-hexan-1-ol

HRID 885161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 885161
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C@@H:10]([NH2:24])[CH2:11][CH2:12][CH:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14]([F:17])([F:16])[F:15].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[NH2:24][C@@H:10]([CH2:11][CH2:12][CH:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14]([F:15])([F:16])[F:17])[CH2:9][OH:8]

Komponenten

5

Edukt 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 67177271(S)-2-Amino-6,6,6-trifluoro-5-phenyl-hexanoic acid methyl ester

Produkt 1

HCID 67177841(S)-2-Amino-6,6,6-trifluoro-5-phenyl-hexan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a suspension of lithium aluminum hydride (0.267 g) in tetrahydrofuran (30 ml) was added a solution of (S)-2-amino-6,6,6-trifluoro-5-phenyl-hexanoic acid methyl ester (0.97 g) in tetrahydrofuran (3 ml) and the mixture was stirred for 2 hours at 50° C. Sodium sulphate solution (2M, 0.3 ml) was added and the mixture was filtered through Celite. The solvent was evaporated and the residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/MeOH=98:2) to yield a light yellow liquid, (0.50 g, 57%); MS (ISP): 248.1 ((M+H)+).

Aufarbeitung

  1. filtrationthe mixture was filtered through Celite
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/MeOH=98:2)
  4. customto yield a light yellow liquid, (0.50 g, 57%)

Quellen und Nachweise

ORD-Eintrag
ord-d57cf859de8e4fbda7f507f15b894e36
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242153B2

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