Dicyclohexylcarbodiimide → HCID 60142174, compound

Participants

Reaction Conditions

Reaction Steps

3-Pyrrolidin-1-yl-propionic acid (143 mg, 1.0 mmol) and dicyclohexylcarbodiimide (247 mg, 1.2 mmol) were dissolved in dichloromethane (5 mL). Subsequently, 4-dimethylaminopyridine (97 mg, 0.8 mmol) and (3aS,4R,7aS)-4-hydroxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester (250 mg, 0.8 mmol) were added. The resulting suspension was stirred at room temperature (22° C.) for 50 h. The precipitation was then removed by filtration and the clear filtrate was subjected to silica gel flash chromatography [ISCO CombiFlash Companion; 40 g silica gel; methylenechloride/methanol; methanol 0% (4 min), 1% (4 min), 2% (4 min), 2-5% (2 min), 5% (5 min) and 10% (8 min)]. Then, the solvents were evaporated to yield (3aR,4S,7aR)-4-(3-pyrrolidin-1-yl-propionyloxy)-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester (123 mg, 0.28 mmol, 35% yield). MS [M+H]=439; RT=6.122 min (LC-MS Method III). 1H-NMR (600 MHz; DMSO-d6) ppm 1.23 (m, 1H), 1.65 (broad s, 4H), 1.80 to 2.10 (m, 5H), 2.30 (s, 3H), 2.46 (m, 4H), 2.49 (m, 4H), 2.67 (m, 2H), 3.13 (m, 1H), 3.30 (m, 1H), 3.42 (q, 1H), 3.55 (s, 3H), 3.88 (m, 1H), 7.22 (broad s, 2H) and 7.27 (m, 2H).

Provenance & Evidence