Phosphorus trichloride → HCID 88037653, compound

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.

1. temperatureThe resulting mixture was then refluxed for 2 days
2. customto give the crude (S, S)-2,5-dimethyl-1-N(4′-dichlorophosphinophenyl)pyrrolidine (31P NMR: δ165.8 (s) ppm)
3. customAfter precipitates (Py. HCl)
4. filtrationwere filtered off
5. customthe excess PCl3 and pyridine solvent were removed from filtrates
6. additiona mixture of 10 mL of pyridine and 20 mL of THF
7. additionwas added to the resulting residue
8. stirringThe resulting suspension was stirred at room temperature overnight before the solution
9. filtrationwas filtered off
10. washThe resin was washed with THF (2×10 mL), hexane (3×10 mL), CH2Cl2 (4×10 mL), and hexane (2×10 mL)
11. customThe resulting resin was dried in vacuum overnight

ORD record

ord-32fe4aa5fefe48e89affeec48a8719d2

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06716984B2