Methanol → HCID 11984447, compound

A solution of (5S)-6-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-3-oxo-hexanoic acid tert-butyl ester (20 g, 0.044 mol) in THF (60 mL) was stirred under nitrogen and methanol (20 mL) was added. The reaction mixture was stirred for 15 min. and cooled to −50° C. to −55° C. Anhydrous CeCl3 (10.8 g, 0.044 mol) was added and stirred for 30 min., maintaining the temperature between −50 and −55° C. Sodium borohydride (2.5 g, 0.066 mol) was added in 6 portions maintaining the temperature between −70 and −90° C. The resulting mixture was stirred for 6 h at the same temperature. After warming the reaction mixture to RT, it was concentrated to a residue under vacuum at about 45° C. Methanol (60 mL) was added and the resulting mixture was concentrated. The resulting residue was cooled to RT, water (50 mL) was added and the resulting aqueous mixture was extracted with ethyl acetate (100 mL×2). The combined organic layer was washed with brine solution (50 mL), and concentrated to obtain the title compound. Yield: 17 g.

1. temperaturecooled to −50° C. to −55° C
2. stirringstirred for 30 min.
3. temperaturemaintaining the temperature between −50 and −55° C
4. temperaturemaintaining the temperature between −70 and −90° C
5. stirringThe resulting mixture was stirred for 6 h at the same temperature
6. concentrationit was concentrated to a residue under vacuum at about 45° C
7. additionMethanol (60 mL) was added
8. concentrationthe resulting mixture was concentrated
9. temperatureThe resulting residue was cooled to RT
10. additionwater (50 mL) was added
11. extractionthe resulting aqueous mixture was extracted with ethyl acetate (100 mL×2)
12. washThe combined organic layer was washed with brine solution (50 mL)
13. concentrationconcentrated

ORD record

ord-1557a6dcd691446bb992e33641f47fa5

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07232920B2