تفاعل #1053709

معادلة التفاعل

5-(2-methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester

5-(2-Methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester

N-methylcyclohexylamine

→

desired product

المردود 60.0%

5-[2-(Cyclohexyl-methyl-amino)-ethyl]-2-methyl-1H-indole-3-carboxylic acid benzyl ester

المردود 60.0%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىpartitioned between methylene chloride and water
2. 2
   غسيلThe organic phase was washed with water and brine
3. 3
   تجفيفdried over Na2SO4
4. 4
   ترشيحfiltered
5. 5
   تركيزThe filtrate was concentrated in vacuo
6. 6
   أخرىto give a solid residue, which
7. 7
   أخرىwas purified by chromatography (5%-15% methanol in methylene chloride)

الإجراء التجريبي

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.

المصدر