Trifluoroacetic acid → HCID 59846007, compound

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Reaction Steps

The faster running isomer of tert-butyl (2R)-2-{[4-(3,4-dichlorophenyl)piperazin-1-yl]carbonyl}-4-(4-hydroxy-4-pyridin-2-ylcyclohexyl)piperazine-1-carboxylate (45 mg) was dissolved in dichloromethane (6 ml). Trifluoroacetic acid (1 ml) was added and the solution stirred at room temperature for 2 hours and allowed to stand over the weekend. The mixture was partitioned between saturated aqueous sodium bicarbonate (10 ml) and dichloromethane (2×100 ml) and combined organics were concentrated in vacuo and adsorbed onto silica for purification by chromatography eluting with 0-15% methanol/dichloromethane. This gave one isomer of 4-((3R)-3-{[4-(3,4-dichlorophenyl)piperazin-1-yl]carbonyl}piperazin-1-yl)-1-pyridin-2-ylcyclohexanol as a light brown solid (31%, 85%).

Provenance & Evidence