Ethyl Acetate → HCID 86686252, compound

tert-Butyl 3-{[6-(hydroxymethyl)pyridin-3-yl]oxy}azetidine-1-carboxylate (242 mg) and THF (3 ml) were mixed, and triethylamine (182 mg) and methanesulfonyl chloride (147 mg) were added thereto, followed by stirring at room temperature for 1 hour. In another flask, THF (3 ml) and EtOH (237 mg) were mixed, and NaH was added thereto, followed by stirring at room temperature for 10 minutes. The reaction mixture prepared immediately before was added thereto, followed by stirring at room temperature for 1 hour. Water and EtOAc were added to the reaction mixture, and the organic layer was concentrated under reduced pressure. DCE (4 ml) and TFA (1 ml) were added to the obtained residue, followed by stirring at room temperature for 5 hours, and then concentrating under reduced pressure. CHCl3 and a 1M aqueous NaOH solution were added to the residue, and the organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain 5-(azetidin-3-yloxy)-2-(ethoxymethyl)pyridine (131 mg).

1. stirringby stirring at room temperature for 10 minutes
2. customThe reaction mixture prepared immediately
3. additionbefore was added
4. stirringby stirring at room temperature for 1 hour
5. concentrationthe organic layer was concentrated under reduced pressure
6. additionDCE (4 ml) and TFA (1 ml) were added to the obtained residue
7. stirringby stirring at room temperature for 5 hours
8. concentrationconcentrating under reduced pressure
9. additionCHCl3 and a 1M aqueous NaOH solution were added to the residue
10. dry with materialthe organic layer was dried over Na2SO4
11. concentrationconcentrated under reduced pressure
12. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

ORD record

ord-a5a77cb3949a4464bf83f2e7c961b27c

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09051283B2