Carbamic acid, [(1R)-3-hydroxy-1-methylpropyl]-, 1,1-dimethylethyl ester (9CI)

159877-47-1

167216-17-3

General procedure for the synthesis of tert-butyl (R)-(4-hydroxybutan-2-yl)carbamate from methyl (R)-N-Boc-3-aminobutyrate: To a solution of methyl (R)-3-((tert-butoxycarbonyl)amino)butyrate (3.0 g, 14.76 mmol) in tetrahydrofuran (THF) (50 mL) was slowly added lithium aluminum (0.728 g, 19.19 mmol) hydroxide (0.728 g, 19.19 mmol) at -78°C under nitrogen protection. Lithium aluminum hydride (0.728 g, 19.19 mmol) was added slowly at -78°C under nitrogen protection. The reaction mixture was stirred at this temperature for 1 hour. Subsequently, the reaction system was slowly warmed to 0°C and the reaction was quenched by dropwise addition of water (0.7 mL) and 15% NaOH aqueous solution (0.7 mL). After quenching, the mixture was stirred at room temperature for 1 h and then filtered through a diatomaceous earth pad. The filtrate was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give tert-butyl (R)-(4-hydroxybutan-2-yl)carbamate (1.3 g).