Diisobutylaluminumhydride → 1-(piperidin-4-yl)-2,3-dihydro-1H-imidazol-2-one

Diisobutylaluminum hydride (1M, 0.875 μL, 0.875 mmol) was added to a solution of methyl N-{[(1-(tert-butoxycarbonyl)piperidin-4-yl)amino]carbonyl}glycinate (230 mg, 0.729 mmol) in toluene (5 μL) and dichloromethane (5 mL) at −78° C. and stirred for 30 min and then warmed to ambient temperature. After 30 min at room temperature, the reaction was quenched with 1 N saturated potassium sodium tartrate solution (15 mL) and extracted with dichloromethane (2×). The combined organic extracts were dried over sodium sulfate, filtered, concentrated. The crude material was dissolved in dichloromethane (10 μL) and treated with trifluoroacetic acid (5 mL). After 25 min, the reaction was concentrated to give the title compound. MS 168.3 (M+1)

1. waitAfter 30 min at room temperature
2. customthe reaction was quenched with 1 N saturated potassium sodium tartrate solution (15 mL)
3. extractionextracted with dichloromethane (2×)
4. dry with materialThe combined organic extracts were dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. dissolutionThe crude material was dissolved in dichloromethane (10 μL)
8. additiontreated with trifluoroacetic acid (5 mL)
9. waitAfter 25 min
10. concentrationthe reaction was concentrated

ORD record

ord-f2fd470f35264d57a008477da39ecfd9

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07632832B2