N-Methylcyclohexylamine → HCID 10111866, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(2-methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (400 mg, 1.03 mmol, Example 56, Step D) in dioxane (10 mL) was added N-methylcyclohexylamine (1.3 mL, 10.3 mmol). The mixture was stirred at 80° C. overnight and then partitioned between methylene chloride and water. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give a solid residue, which was purified by chromatography (5%-15% methanol in methylene chloride) to give 250 mg (60%) of the desired product as a white solid: mp 122-124° C.; MS(APCI+): m/z 405.2 (MH+); Anal. Calcd for C26H32N2O2.0.5H2O: C, 75.51; H, 8.04; N, 6.77. Found: C, 75.25; H, 8.04; N, 6.78.

Provenance & Evidence