Trimethylphosphine → HCID 131734125, compound

Participants

Reaction Steps

tert-butyl ((3S)-1-(4-isothiocyanato-5-isothiazolyl)-3-piperidinyl)carbamate. A dry, 25 mL pear flask was charged with tert-butyl ((3S)-1-(4-azido-5-isothiazolyl)-3-piperidinyl)carbamate (213 mg, 0.66 mmol), a stirbar, and dry THF (4 mL). The flask was fitted with a septa/Ar inlet and immersed into a ice-water bath. The solution was stirred for 10 min and a 1.0 M solution of PMe3 in THF (0.69 mL, 0.69 mmol) was added dropwise. The solution was stirred cold for 15 min. The solution was taken up into a 5 mL syringe (total volume=4.4 mL) to afford (S)-tert-butyl (1-(3-((trimethylphosphoranylidene)amino)isothiazol-5-yl)piperidin-3-yl)carbamate. A dry, 25 mL pear flask was charged with dry THF (2 mL), carbon disulfide (0.79 mL, 13.11 mmol), and a stirbar. The flask was fitted with a septa/Ar inlet/PTFE addition needle and immersed into an ice-water bath. The solution was stirred for 15 min. The syringe containing (S)-tert-butyl (1-(3-((trimethylphosphoranylidene)amino)isothiazol-5-yl)piperidin-3-yl)carbamate, as described above, was fitted to the PTFE addition needle. The solution was added via syringe pump over a 1 h period. The solution was stirred for 1 h, and concentrated in vacuo. The residue was dried in a vacuum oven (60° C., <1 mm Hg) for 1 h to afford tert-butyl ((3S)-1-(4-isothiocyanato-5-isothiazolyl) -3-piperidinyl)carbamate. The material was used without characterization.

Provenance & Evidence