Sodium cyanoborohydride → HCID 86684460, compound

Temperature

50 °C

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 243e (2.2 g, 6.3 mmol), NaBH3CN (995 mg, 15.8 mmol), oxetan-3-one (907 mg, 12.6 mmol), zinc chloride (2.1 g, 15.8 mmol), and methanol (60 mL). The reaction mixture was stirred at 50° C. for 5 hrs and concentrated under reduced pressure. To the residue was added water and the resulting mixture was extracted with dichloromethane three times. The combined organic layer was then concentrated under reduced pressure and the resulting residue was purified by silica-gel column chromatography eluting with 1% triethylamine in methanol. The fractions containing the desired product were concentrated under reduced pressure. Dichloromethane was added to the residue and the resulting suspension was filtered. The filtrate was concentrated under reduced pressure afford 243f as a yellow solid (800 mg, 62%). MS-ESI: [M+H]+ 408.2

1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
2. concentrationconcentrated under reduced pressure
3. additionTo the residue was added water
4. extractionthe resulting mixture was extracted with dichloromethane three times
5. concentrationThe combined organic layer was then concentrated under reduced pressure
6. customthe resulting residue was purified by silica-gel column chromatography
7. washeluting with 1% triethylamine in methanol
8. additionThe fractions containing the desired product
9. concentrationwere concentrated under reduced pressure
10. additionDichloromethane was added to the residue
11. filtrationthe resulting suspension was filtered
12. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-4ba48f623a464246a421204ae25a303a

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716274B2