Triethylamine → (2S,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrate

HRID 703273

Reaktionsgleichung

Reaktionsgleichung von HRID 703273
[C:1]([NH:9][CH2:10][CH:11]([C:16](=[O:18])[CH3:17])[C:12]([O:14][CH3:15])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC>C(Cl)Cl.[Ru]>[C:1]([NH:9][CH2:10][C@@H:11]([C@H:16]([OH:18])[CH3:17])[C:12]([O:14][CH3:15])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 8471TriethylamineHCID 11831808Methyl 2-((benzoylamino)methyl)-3-oxobutanoate

Produkt 1

HCID 10060699(2S,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23950RutheniumKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In a 100 ml-volume stainless steel-made autoclave whose atmosphere had been displaced with nitrogen was charged a solution of 2.5 g (10 mmole) of methyl 2-(N-benzoylamino)methyl-3-oxobutanoate and 84.5 mg (0.05 mmole) of the ruthenium-optically active phosphine complex as synthesized in Reference Example 1 [Ru2Cl4 ((+)-BINAP)2 (NEt3)] in 17.5 ml of methylene chloride, and the mixture was stirred at 50° C. under a hydrogen pressure of 100 kg/cm2 for 20 hours to conduct a hydrogenation reaction. The solvent was removed from the reaction mixture by distillation, and the residue was purified by silica gel column chromatography using a mixed solvent of n-hexane and ethyl acetate as an eluent to obtain 2.25 g (yield: 90%) of methyl (2S, 3R)-2-(N-benzoylamino)methyl-3-hydroxybutanoate having an optical purity of 98 %ee.

Aufarbeitung

  1. customa hydrogenation reaction
  2. customThe solvent was removed from the reaction mixture by distillation
  3. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4b5c6a4e5cd14134b423e998d4fef81d
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04981992

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