Phosphorus trichloride → HCID 88037653, compound

Participants

Reaction Steps

A solution of PCl3 (5.0 g, 36.4 mm) in 15 mL of pyridine was treated with (S, S)-2,5-dimethyl-1-N-phenylpyrrolidine (0.5 g, 2.87 mm) over a period of 5 min. The resulting mixture was then refluxed for 2 days to give the crude (S, S)-2,5-dimethyl-1-N(4′-dichlorophosphinophenyl)pyrrolidine (31P NMR: δ165.8 (s) ppm). After precipitates (Py. HCl) were filtered off, the excess PCl3 and pyridine solvent were removed from filtrates, a mixture of 10 mL of pyridine and 20 mL of THF was added to the resulting residue. Next, polymer-supported secondary amines from Example 1 (2.0 g, 1.1 mmol/g, 2.2 mmol) was slowly added into the mixture above while stirring at room temperature for a period of 10 min. The resulting suspension was stirred at room temperature overnight before the solution was filtered off. The resin was washed with THF (2×10 mL), hexane (3×10 mL), CH2Cl2 (4×10 mL), and hexane (2×10 mL). The resulting resin was dried in vacuum overnight to yield the polymer-supported (S,S)-2,5-dimethyl-1-N(4′-chlorophosphinophenyl)pyrrolidine. 31P NMR (122 MHz, CDCl3): δ147.6 ppm.

Provenance & Evidence