5,5-DiMethylpiperidin-2-one synthesis

Yield:-

Reaction Conditions:

Stage #1:ethyl 4-cyano-4-methylpentanoate with hydrogen;acetic acid;platinum(IV) oxide under 4137.29 - 6205.94 Torr;Inert atmosphere;
Stage #2: with sodium hydroxide in water

Steps:

C6.2
Example C6, Step 2: The mixture of the cyano-ester starting material (e.g., ethyl 4- cyano-4-methylpentanoate, 30 mmol) and ΡΚ¾ (65 mg) in AcOH (10 mL) was purged with N2 three times, then subjected to hydrogen gas to at 80 to 120 Psi until hydrogen uptake stopped. The catalyst was filtered and rinsed with EtOAc. The filtrate was slowly added into 6N NaOH (aq), then diluted with EtOAc. The aqueous layer was extracted with additional EtOAc. The combined organic layer was washed with brine and concentrated to give the desired lactam product (e.g. 5,5-dimethylpiperidin-2-one, 84% yield).

References:

HEFFERNAN, Michele, L., R.;HARDY, Larry, Wendell;WU, Frank, Xinhe;SARASWAT, Lakshmi, D.;SPEAR, Kerry, L. WO2012/170845, 2012, A2 Location in patent:Page/Page column 95