Tetrahydrofuran → 2-((2S,3R)-3-(3-chlorophenyl)-2-(4-chlorophenyl)-6-oxopiperidin-1-yl)pentanedial

To a solution of 454 mg (1.175 mmol) of (5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopent-2-enyl)piperidin-2-one (Example 104, Step A) in THF (6 mL) was added water dropwise (3.5 mL) and tBuOH (0.2 mL). 4-methylmorpholine 4-oxide (207 mg, 1.763 mmol) was added followed by 4% aq. osmium(VIII) oxide (37.3 μL, 5.88 μmol). The reaction mixture was stirred at room temperature for 18 h. Sodium periodate (704 mg, 3.29 mmol) was added and the cloudy reaction mixture was stirred at room temperature for 90 min. Water (4 mL) was added and the mixture was filtered and washed with EtOAc. The filtrate was diluted with EtOAc and the layers were separated. The combined organic layers were washed with sat. Na2S2O3, sat. aq. NaCl solution, dried over Na2SO4 and concentrated in vacuo to provide the title compound.

1. customthe cloudy reaction mixture
2. stirringwas stirred at room temperature for 90 min
3. filtrationthe mixture was filtered
4. washwashed with EtOAc
5. additionThe filtrate was diluted with EtOAc
6. customthe layers were separated
7. washThe combined organic layers were washed with sat. Na2S2O3, sat. aq. NaCl solution
8. dry with materialdried over Na2SO4
9. concentrationconcentrated in vacuo

ORD record

ord-926c9067c3ab41349da26e1b72cfd7e4

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569341B2