Hydrochloric Acid → HCID 86743651, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-cyclohexyl-isopropyl-amine (2.8 ml: 0.017 mol) in anhydrous THF (120 ml), 11.4 ml (0.016 mol) of a butyllithium solution were added in 30'; the stirred mixture was then cooled (under nitrogen) to -78° C., and 3α,7β-diethoxycarbonyl-12α-hydroxy-5β-cholan-24-oic acid, methyl ester (2.5 g; 0.0045 mol), dissolved in 22 ml of anhydrous THF was added very slowly (45'). Fifteen minutes after the addition, CH3I (10.2 g; 0.072 mol) was added, and the mixture was brought to room temperature. After 5 hours the reaction was complete; the solution was acidified with a 10% aqueous solution of HCl and extracted with CHCl3 (3×80 ml). The chloroform solution was washed with water, dried on Na2SO4, and evaporated to dryness. The yield is almost quantitative.

Provenance & Evidence