Diisopropylamine → HCID 14280468, compound

Participants

Reaction Conditions

Reaction Steps

199 mg (1.97 mmol) of diisopropylamine was dissolved in 2.5 ml of dry tetrahydrofuran, and in an atmosphere of nitrogen, 0.795 ml of n-butyllithium (1.65N hexane solution) was added dropwise at 1° C., and the mixture was maintained at 1° C. for 45 minutes. To the reaction mixture were added dropwise at 1° C. 68.7 mg (0.438 mmol) of (S)-(-)-prolinol propionamide and 0.5 ml of dry tetrahydrofuran, and the mixture was reacted at room temperature for 1 hour. To the reaction mixture was added dropwise 0.2 ml (1.15 mmol) of dry HMPA, and the mixture was cooled to -100° C. Then, 112 mg (0.29 mmol) of the compound (8) was dissolved in 0.5 ml of dry tetrahydrofuran, and reacted at -100° C. for 11 hours, and left to stand at -80° C. for 4 days. Water was added to the reaction mixture, and the mixture was extracted with ether. The ethereal layer was washed with 1N hydrochloric acid and an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by chromatography (Wako Gel C-200 (3 g), hexane/ether/methanol) to give 97.0 mg (yield 86.6%) of compound (9).

Provenance & Evidence