HCID 22940645, compound → Ammonia

Participants

Reaction Steps

Nitrile 10-3 (9.48 g, 24.2 mmol) was dissolved in 200 mL i-PrOH sat. with NH3.5% Rh on alumina (10.69 g) was added, and the mixture was hydrogenated on a Parr shaker at 50 psi H2 pressure. After 3 d, the reaction mixture was filtered through Celite, re-saturated with NH3, treated with fresh 5% Rh on alumina (3.00 g), and hydrogenated at 50 psi for 1 d more. After filtering through Celite, the mixture was concentrated and purified by flash chromatography (silica, CH2Cl2, then 10%, 20%, then 30% NH3 sat. EtOH/CH2Cl2) to provide the lactam 10-4 as a crystalline yellow solid.

Provenance & Evidence