tert-butyl N-methyl-N-(2-oxoethyl)carbamate → HCID 68409171, compound

A solution of 4.73 g (1 eq) tert-butyl methyl(2-oxoethyl)carbamate in 20 ml methanol was added to a solution of 7 g (1 eq) 4-butyl-N,N-dimethylpiperidin-4-amine bis hydrochloride in 50 ml methanol at room temperature and the reaction mixture obtained was stirred for 50 min at room temperature. 3.43 g (2 eq) sodium cyanoboron hydride were added in portions to this reaction mixture and it was then stirred for 12 h at room temperature. The reaction course was monitored by thin-layer chromatography (20% MeOH/CHCl3). Once the conversion was complete, the reaction mixture was cooled to 0° C. and adjusted to a pH of ˜5 with acetic acid. 2 g tert-butyl formylmethyl methylcarbamate and 1.7 g sodium cyanoboron hydride were again added and the reaction mixture was stirred for a further 60 min at room temperature. The methanol was then distilled off, 100 ml saturated NaHCO3 solution were added and the mixture obtained was extracted with ethyl acetate (2×200 ml) and the combined organic phases were dried over Na2SO4. Following removal of the solvent under reduced pressure, 10.5 g of crude product were obtained in the form of a pale yellow oil.

1. customthe reaction mixture obtained
2. stirringwas then stirred for 12 h at room temperature
3. temperaturethe reaction mixture was cooled to 0° C.
4. stirringthe reaction mixture was stirred for a further 60 min at room temperature
5. distillationThe methanol was then distilled off
6. addition100 ml saturated NaHCO3 solution were added
7. customthe mixture obtained
8. extractionwas extracted with ethyl acetate (2×200 ml)
9. dry with materialthe combined organic phases were dried over Na2SO4
10. customremoval of the solvent under reduced pressure

ORD record

ord-0951b473f9b14e129e9da226b87be985

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206156B2