p-Toluenesulfonic acid → HCID 131730843, compound

Participants

Reaction Steps

10% Pd/C (Degussa, 50% wet, 0.87 g) was carefully wetted down under argon with ethanol, then (1S,2R)-ethyl 2-((R)-1-phenylethylamino)cyclohexane-carboxylate, tosylic acid (8.7 g, 19.4 mmol) in ethanol (75 mL) was added. The mixture was then hydrogenated for 20 hours at 50 psi in a Parr shaker apparatus. Under argon, the catalyst was filtered off. The filtrate was resubjected to hydrogenation, this time with 1.70 grams of 10% Pd/C (Degussa, 50% wet). After 6 hours, the reaction was analyzed by LCMS, which detected little change. Under argon, the reaction was carefully filtered through a fiberglass filter paper. The filtrate was concentrated to give a colorless oil. The oil was resubjected to 10% Pd/C (Degussa, 50% wet, 1.70 grams) in 50 mL of ethanol and hydrogenated for 20 hours at 50 psi. Under argon, the reaction was carefully filtered through a fiberglass filter paper. The filtrate was concentrated to give (1S,2R)-ethyl 2-aminocyclohexanecarboxylate tosylic acid (5.4 g, 15.7 mmol, 81% yield) as a colorless oil. MS (ESI+)=172.16 (M+H)+.

Provenance & Evidence