Triethylamine → HCID 54560404, compound

Temperature

-78 °C

N-Methyl-N-((1R)-2-methylamino-1-((2-thienyl)methyl)ethyl)carbamic acid tert-butyl ester (1.72 g, 6.05 mmol) was dissolved in dichloromethane (30 ml). Triethylamine (0.84 ml, 6.05 mmol) was added. The solution was cooled to −78° C. Methanesulfonyl chloride (0.47 ml, 6.05 mmol) was added dropwise. The reaction mixture was warmed to room temperature over a period of 3.5 h. It was stirred at room temperature for 16 h. The reaction mixture was diluted with dichloromethane (100 ml). It was washed with 10% aqueous sodium hydrogen sulfate solution (200 ml). The aqueous phase was extracted with dichloromethane (2×50 ml). The combined organic layers were washed with saturated sodium hydrogen carbonate solution (200 ml) and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (180 g), using ethyl acetatelheptane 1:1 as eluent, to give 1.94 g of N-methyl-N-((1R)-2-(N-methyl-N-(methylsulfonyl)amino)-1-((2-thienyl)methyl)ethyl)carbamic acid tert-butyl ester.

1. temperatureThe reaction mixture was warmed to room temperature over a period of 3.5 h
2. washIt was washed with 10% aqueous sodium hydrogen sulfate solution (200 ml)
3. extractionThe aqueous phase was extracted with dichloromethane (2×50 ml)
4. washThe combined organic layers were washed with saturated sodium hydrogen carbonate solution (200 ml)
5. dry with materialdried over magnesium sulfate
6. customThe solvent was removed in vacuo
7. customThe crude product was purified by flash chromatography on silica (180 g)

ORD record

ord-b89d47a8c0f34cd181f19e8eefa23c2d

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06939880B2