Acetic Acid → HCID 86662316, compound

Temperature

50 °C

To a large capacity microwave tube containing 2-(6-chloropyridin-3-yloxy)-2-methylpropanal (354 mg, 1.77 mmol) and sodium triacetoxyborohydride (940 mg, 4.43 mmol) in dry dichloromethane (4 ml) was added glacial acetic acid (0.81 ml, 14.2 mmol) followed by a 2 M solution of dimethylamine (14.2 ml, 28.4 mmol, in tetrahydrofuran). The tube was capped and heated to 50° C. (oil bath) with vigorous stirring for 16 hours. The mixture was cooled to ambient and the contents poured into a separatory funnel containing an aqueous solution of saturated sodium bicarbonate (30 ml). Dichloromethane (30 ml) was added and the mixture was shaken. The contents were filtered through a plug of celite, washing well with dichloromethane. The filtrate was collected and washed with a brine solution (40 ml). The dichloromethane phase was collected and the aqueous phase was back extracted with methylene chloride (2×40 mL). The organic phases were combined, dried over magnesium sulfate, filtered and stripped. The material was purified by preparative thin layer chromatography (2 plates), eluting with 1.8% methanol/dichloromethane. The plates were then re-developed with 2.6% methanol/dichloromethane, and the product band was collected which provided the desired as a light yellow mobile oil, which slowly solidified on standing (255 mg). (M+H)+=229 m/e.

1. customThe tube was capped
2. temperatureThe mixture was cooled to ambient and the contents
3. additionpoured into a separatory funnel
4. stirringthe mixture was shaken
5. filtrationThe contents were filtered through a plug of celite
6. washwashing well with dichloromethane
7. customThe filtrate was collected
8. washwashed with a brine solution (40 ml)
9. customThe dichloromethane phase was collected
10. extractionthe aqueous phase was back extracted with methylene chloride (2×40 mL)
11. dry with materialdried over magnesium sulfate
12. filtrationfiltered
13. customThe material was purified by preparative thin layer chromatography (2 plates)
14. washeluting with 1.8% methanol/dichloromethane
15. customre-developed with 2.6% methanol/dichloromethane, and the product band was collected which
16. customprovided the

ORD record

ord-42a30b7594344b2f9ff7cbfc6d834566

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481540B2