(S)-TERT-LEUCINOL

Chemical Properties

Uses

reaction suitability

Synthesis

20859-02-3

112245-13-3

GENERAL STEPS: Example 8-1; To a 100 mL Schlenk tube purged with nitrogen was added 4.00 g (30.5 mmol) of (S)-tert-leucine and 40 mL of tetrahydrofuran, and the temperature of the reaction system was adjusted to 10°C. Over 5 min, 1.46 g (61.0 mmol) of lithium borohydride was added to the suspension in batches, followed by adjusting the temperature of the system to 20 °C. Over 30 minutes, 7.44 g (67.1 mmol) of trimethylmethylsilyl chloride was added slowly and dropwise, then the mixture was heated to 65 °C and stirred continuously at this temperature for 3 hours. Upon completion of the reaction, the mixture was cooled to 10 °C and quenched by the slow dropwise addition of 4 mL of methanol over 20 min. After concentrating the reaction mixture using a rotary evaporator, 40 mL of 4 M aqueous sodium hydroxide solution was added and stirred for 1 hour at room temperature. Subsequently, 40 mL of tert-butyl methyl ether was added for extraction and the organic layer was separated and dried with anhydrous sodium sulfate. After filtration to remove the desiccant, the tert-butyl methyl ether was removed by atmospheric pressure distillation. Finally, the 70 to 75 °C fraction was collected by reduced pressure distillation (0.3 kPa) to give 2.96 g of (S)-tert-leucinol in 83% yield.

References