Pyridine → Tert-butyl 6-methyl-1,2,3-oxathiazinane-3-carboxylate 2-oxide

To a stirred solution of thionyl chloride (2.0 mL, 27.9 mmol) in acetonitrile (15 mL) cooled to −45° C. is added a solution of tert-butyl (3-hydroxybutyl)carbamate (2.1 g, 11.2 mmol) in acetonitrile (20 mL) by syringe over 10 min, keeping the internal temperature below −40° C. 4-Dimethylaminopyridine (136 mg, 1.1 mmol) is added followed by the dropwise addition of pyridine (4.5 mL, 55.8 mmol, keeping the temperature below −40° C. The addition takes 90 min. Ethyl acetate (50 mL) is added to the suspension and the mixture is filtered at −35° C. to remove the solid and the solid which is washed with EtOAc before it is discarded. The filtrates are combined, and saturated Na2HPO4 solution (20 mL) is added. The mixture is stirred vigorously for 30 min and the organic layer is separated, washed with 1M NaHSO4 to remove residual pyridine, dried (MgSO4) and concentrated to afford the title compound (2.52 g, 96%) as an oil.

1. customthe internal temperature below −40° C
2. customthe temperature below −40° C
3. additionThe addition
4. filtrationthe mixture is filtered at −35° C.
5. customto remove the solid
6. washthe solid which is washed with EtOAc before it
7. additionsaturated Na2HPO4 solution (20 mL) is added
8. customthe organic layer is separated
9. washwashed with 1M NaHSO4
10. customto remove residual pyridine
11. dry with materialdried (MgSO4)
12. concentrationconcentrated

ORD record

ord-32929acc298e41ba97af5407456de97d

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150577B2