Sodium Hydroxide → HCID 22630148, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ester 48 (0.9 g, 2.95 mmol) in DMSO (10 ml) was added water (0.53 ml, 2.95 mmol) and lithium chloride (0.25 g, 5.9 mmol). The mixture was stirred for 3 h at 175-180° C., then it was cooled and water (30 ml) was added. The mixture was extracted with diethyl ether. The extract was washed with water and with brine, dried over anhydrous MgSO4, filtered and concentrated to 10 ml volume. The solution obtained was added dropwise to a suspension of lithium aluminum hydride (0.25 g, 6.6 mmol) in diethyl ether (15 ml) and stirred at reflux for 3 h. The mixture was cooled and treated with 20% aqueous NaOH, and extracted with diethyl ether. The extract was washed with brine, dried over NaOH, filtered and treated with anhydrous HCl solution in diethyl ether. After evaporation of the solvent, the residue was purified by chromatography on silica gel (chloroform-methanol, 20:1) to give 49 (0.245 g, 31%) as a colorless solid. 1H NMR (DMSO-D6, TMS): 0.92, 0,96 and 1.04 (total 15H, all s, 3′,5′-CH3 and 1′-CH3), 1.00-1.65 (total 6H, m, ring-CH2); 1.85-2.40 (3H, m, 3-CH2, 4-CH); 2.60-3.10 (2H, m, CH2N); 4.90-5.25 (2H, m, ═CH2); 5.62-6.10 (1H, m, ═CH) and 7.92 ppm (3H, br s, NH3+).

Provenance & Evidence