Tert-butyl 2-oxo-2-pyrimidin-2-ylethyl(methyl)carbamate → tert-butyl (2R)-2-hydroxy-2-pyrimidin-2-ylethyl(methyl)carbamate

In a glove box, triethylamine (6.6 g) was added carefully with stirring to formic acid (4.6 g) in a glass vial and stirring was continued until the mixture had cooled to room temperature. A 50 mL Schlenk flask was charged with [(η6C6H6)RuCl2]2 (200 mg), (R)(R)-TsDPEN (350 mg), anhydrous i-PrOH (10 mL), and triethylamine (0.35 mL). The Schlenk flask was removed from the glove box and placed on a Schlenk line, a reflux condenser attached, and the reaction mixture was heated to 75° C. for 1 h under nitrogen. The reaction was then cooled to 0° C. giving a solid which was collected by filtration. The solid was washed with diethyl ether and air-dried giving 228 mg of (η6C6H6)Ru[(R,R)-TsDPEN]Cl. To a 50 mL RB flask in a glove box was added (β6C6H6)Ru[(R,R)-TsDPEN]Cl (17 mg) followed by the mixture of the triethylamine/formic acid solution prepared above. The mixture was allowed to stir at room temperature for 20 min and tert-butyl 2-oxo-2-pyrimidin-2-ylethyl(methyl)carbamate (1.33 g) was added. The mixture was stirred at room temperature for 17 h, poured into water (75 mL), and extracted with EtOAc (3×100 mL). The combined organic layers were washed with 1 M aq. NaHCO3 (50 mL) and brine (50 mL). The organic layer was dried (MgSO4), filtered, and concentrated to afford 1.17 g of the title compound as an oil.

1. customprepared above
2. stirringThe mixture was stirred at room temperature for 17 h
3. extractionextracted with EtOAc (3×100 mL)
4. washThe combined organic layers were washed with 1 M aq. NaHCO3 (50 mL) and brine (50 mL)
5. dry with materialThe organic layer was dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated

ORD-Eintrag

ord-c6e1537deb1e43ae858815496a192909

Quelldatensatz

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06852731B2