Butylamine → N-butyl-2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

온도

42.5 °C

A mixture of tert-butyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (10 grams), methanol (80 ml), n-butyl amine (20 ml) and potassium carbonate (10.6 grams) was heated to 40-45° C. and stirred up to completion of the reaction. The reaction mixture was distilled under reduced pressure and methylene chloride (100 ml) was added to the obtained residue at 25-30° C. and stirred for 15 minutes. The unwanted solid was filtered off and the filtrate was distilled off under reduced pressure. The obtained residue was dissolved in methylene chloride (32 ml) and a mixture of AZADO (0.002 grams), potassium bromide (0.44 grams) in methylene chloride (48 ml) was added to it and stirred for 15 minutes. Sodium hypochlorite solution (20.8 ml) was added to the reaction mixture at −15 to 15° C. and stirred for an hour. After completion of the reaction, the reaction mixture was quenched with sodium thio sulfate solution at below 10° C. Both organic and aqueous layers were separated and aqueous layer extracted with methylene chloride. The solvent from organic layer was distilled off under reduced pressure to get the title compound.

1. distillationThe reaction mixture was distilled under reduced pressure and methylene chloride (100 ml)
2. additionwas added to the obtained residue at 25-30° C.
3. stirringstirred for 15 minutes
4. filtrationThe unwanted solid was filtered off
5. distillationthe filtrate was distilled off under reduced pressure
6. dissolutionThe obtained residue was dissolved in methylene chloride (32 ml)
7. additiona mixture of AZADO (0.002 grams), potassium bromide (0.44 grams) in methylene chloride (48 ml)
8. additionwas added to it
9. stirringstirred for 15 minutes
10. additionSodium hypochlorite solution (20.8 ml) was added to the reaction mixture at −15 to 15° C.
11. stirringstirred for an hour
12. customAfter completion of the reaction
13. customthe reaction mixture was quenched with sodium thio sulfate solution at below 10° C
14. customBoth organic and aqueous layers were separated
15. extractionaqueous layer extracted with methylene chloride
16. distillationThe solvent from organic layer was distilled off under reduced pressure

ORD 기록

ord-b1e476cf4b494e1bb4aba82acbec9360

출처 데이터셋

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08987444B2