1-BOC-2-PHENYL-PIPERIDIN-4-ONE

General procedure: 4-fluorobenzylamine (80.8 mmol, 10.4 g) was dissolved in ethanol (80 ml) and Nmethyl-4-piperidone (80.8 mmol, 9.43 g) was added. Sodium triacetoxyborohydride (161.6 mmol, 35.4 g) was added in portions and the mixture was stirred at room temperature for 4 hours. Sodium hydroxide (aqueous, 5M) was added until pH> 13 and the resulting mixture was stirred for 1 hour and then partitioned between diethyl ether and water. The organic phase was collected and the aqueous phase was extracted once again with diethyl ether. The combined organic phases were dried and evaporated to give the desired intermediate as a yellow oil (17.48 g, 97 %).To a solution of diethyl cyanomethylphosphonate (1.2 g, 6.77 mmol) in THF (10 mL) at 0 C was added NaH (60% in oil, 0.27 g, 6.75 mmol). The mixture was then stirred at 0 C for ca. lh. The resulted suspension was diluted with THF (25 mL). To the suspension 0 C was added asolution of To a solution of tert-butyl 4-oxo-2-phenylpiperidi ne-i -carboxylate (CAS: 849928-30-9, 500 mg, 1.816 mmol) in THF (10 mL) at -78 C was added L-Selectride (2.2 mL, 2.2 mmol). Themixture was then stirred at -78 C for ca. 1 .75h. The reaction was then quenched with 7N NH3 in MeOH at -78 C, and then stirred at -78 C for 5mm. To the mixture was then added satd. aq. NH4CI, and then stirred at room temperature for 1 .5h. The mixture was then extracted with EtOAc.To a solution of tert-butyl 4-oxo-2-phenylpiperidi ne-i -carboxylate (CAS: 849928-30-9, 500 mg, 1.816 mmol) in THF (10 mL) at -78 C was added L-Selectride (2.2 mL, 2.2 mmol). Themixture was then stirred at -78 C for ca. 1 .75h. The reaction was then quenched with 7N NH3 in MeOH at -78 C, and then stirred at -78 C for 5mm. To the mixture was then added satd. aq. NH4CI, and then stirred at room temperature for 1 .5h. The mixture was then extracted with EtOAc.

Molecular Weight:275.34
XLogP3:2.1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:275.15214353
Monoisotopic Mass:275.15214353
Topological Polar Surface Area:46.6
Heavy Atom Count:20
Complexity:366
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes