Reaktion #1605930

Reaktionsgleichung

H2O CCl4 CH3CN

(1S,2R)-1-furan-2-yl-3-methoxy-2-methyl-propyl methylcarbamic acid tert-butyl ester

→

(2S,3R)-2-(tertbutoxycarbonyl-methyl-amino)-4-methoxy-3-methyl-butyric acid

Lösungsmittel

CH3CN

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter 15 minutes
2. 2
   Extraktionextracted with EtOAc (3×10 mL)
3. 3
   WaschenThe combined organic layers were washed successively with saturated aqueous NaHSO3, brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated in vacuo

Vorschrift

To a stirred solution of NalO4 (969.0 mg, 4.5 mmol, 6.0 equiv) in H2O/CCl4/CH3CN (3/2/3, 21 mL) was added RuCl3 (53.0 mg, 0.26 mmol, 0.34 equiv). After stirring for 15 minutes, a solution of ((1S,2R)-1-furan-2-yl-3-methoxy-2-methyl-propyl methylcarbamic acid tert-butyl ester (214.0 mg, 0.76 mmol) in CH3CN (4 mL) was added. After 15 minutes, the mixture was diluted with water (5 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were washed successively with saturated aqueous NaHSO3, brine, dried over Na2SO4, and concentrated in vacuo to give (2S,3R)-2-(tertbutoxycarbonyl-methyl-amino)-4-methoxy-3-methyl-butyric acid (180.0 mg).

Quelle