HCID 57751157, compound → HCID 67495519, compound

Participants

Reaction Steps

(R)—N′-(1-Cyclohexyl-but-3-enyl)-N′-(3,5-dimethyl-benzoyl)-hydrazine carboxylic acid benzyl ester (2.91 g, 6.7 mmoles) was suspended in ca. 50 mL glacial acetic acid. 102 mg 10% palladium on charcoal was added as a slurry in several mL of acetic acid. The mixture was diluted with acetic acid to 75 mL, and shaken on a Parr hydrogenator for 90 minutes at 20-30 psi. The suspension was allowed to stand for two days to allow the carbon to settle out. The supernatant was filtered through a 0.45 micron syringe filter into a recrystallizing dish and solvent was evaporated to leave 2.06 g (102% mass balance) of (R)-3,5-dimethyl-benzoic acid N-(1-cyclohexyl-butyl)-hydrazide as a reddish brown viscous oil. Rf=0.24 (2:1 hexanes:ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 7.05 (1H, s), 7.0 (2H, s), 4.55+3.35 (1H, 2 t), 2.4 (6H, s), 0.8-1.9 (15H, m), 0.9 (3H, t); HRMS (ESI) m/z calcd for C19H31N2O [M+H]+ 303.2436, found 303.2441, calcd for C19H30N2NaO [M+Na]+ 325.2256, found 325.2262.

Provenance & Evidence