Binap, (A+-)- → HCID 10084691, compound

Temperature

160 °C

A mixture of spiro[1-azabicyclo[2.2.1]heptane-2,3′-pyrrolidine] (50 mg, 0.3 mmol) tris(dibenzylideneacetone)dipalladium(0) (9 mg, 0.009 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (12 mg, 0.018 mmol), potassium tert-butoxide (147 mg, 1.2 mmol), and 5-bromo-3-ethoxypyridine (73 mg, 0.36 mmol) in dry toluene (5 mL) was placed in a sealed tube under argon and heated at 160° C. for 17 h. The reaction was cooled to 0° C. and the contents transferred to a 100 mL round bottom flask. The solvent was removed by rotary evaporation and the residue was dissolved in a saturated solution of NaHCO3 (10 mL) and extracted with chloroform (4×15 mL). The combined chloroform extracts were dried (K2CO3), filtered and concentrated by rotary evaporation to give a dark colored syrup. This was purified by column chromatography, using MeOH:CHCl3:NH4OH (8:2:0.01, v/v) as the eluent, to give 28 mg (27%) of 1′-(5-ethoxy-3-pyridyl)-spiro[1-azabicyclo[2.2.1]heptane-2,3′-pyrrolidine] as a viscous brown oil.

1. customwas placed in a sealed tube under argon
2. temperatureThe reaction was cooled to 0° C.
3. customthe contents transferred to a 100 mL round bottom flask
4. customThe solvent was removed by rotary evaporation
5. dissolutionthe residue was dissolved in a saturated solution of NaHCO3 (10 mL)
6. extractionextracted with chloroform (4×15 mL)
7. dry with materialThe combined chloroform extracts were dried (K2CO3)
8. filtrationfiltered
9. concentrationconcentrated by rotary evaporation
10. customto give a dark colored syrup
11. customThis was purified by column chromatography

ORD record

ord-1b4982a4f4cc48428365661e342f6471

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923559B2