Ammonia → HCID 16495154, compound

A mixture of 6-methyl-pyridine-2-carboxaldehyde (500 mg), titanium (IV) isopropoxide (2.14 g), 2M ethylamine (in THF) in dry THF (12 mL) was stirred for 8 h at RT under nitrogen. Then NaBH4 (428 mg) and EtOH (4 mL) were added, the stirring at RT was continued for 7 h. The reaction mixture was then poured into aqueous ammonia (2M), the resulting inorganic precipitate was filtered and washed with ether. The organic layer was separated and the remaining aqueous layer was extracted with ether. The combined organic extracts were washed with 1M HCl to separate the neutral materials. The acidic aqueous solution was washed once with ether to separate the non-basic impurities, then treated with 2M NaOH to pH 10-12, and extracted with DCM (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give 100 mg (16%) of the title compound which was used for the next step without further purification.

1. waitthe stirring at RT was continued for 7 h
2. filtrationthe resulting inorganic precipitate was filtered
3. washwashed with ether
4. customThe organic layer was separated
5. extractionthe remaining aqueous layer was extracted with ether
6. washThe combined organic extracts were washed with 1M HCl
7. customto separate the neutral materials
8. washThe acidic aqueous solution was washed once with ether
9. customto separate the non-basic impurities
10. additiontreated with 2M NaOH to pH 10-12
11. extractionextracted with DCM (3×)
12. washThe combined organic extracts were washed with brine
13. dry with materialdried over MgSO4
14. filtrationfiltered
15. concentrationconcentrated in vacuo

ORD record

ord-ab4aec62876c4f88abeccdd7ac66ba0e

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003654B2