Synthesis
The general procedure for the synthesis of (S)-2-amino-4-(methylthio)butan-1-ol from L-methionine is as follows (refer to Examples 1-46): 38 mL (300 mmol) of chlorotrimethylsilane was added slowly and dropwise to 200 mL of an anhydrous tetrahydrofuran suspension containing 3.3 g (150 mmol) of lithium borohydride under ice bath cooling conditions. The reaction mixture was stirred for 30 min and then 7.5 g (50 mmol) of L-methionine was added gradually, followed by continued stirring at room temperature overnight. Upon completion of the reaction, methanol was slowly added under ice bath cooling conditions until hydrogen release ceased. Subsequently, the solvent was removed by distillation under reduced pressure. To the residue, 10% sodium hydroxide solution was added and then extracted twice with chloroform. The chloroform extracted layers were combined, dried with anhydrous sodium sulfate and finally the solvent was removed by distillation under reduced pressure to give 5.12 g (75% yield) of the target product (S)-2-amino-4-(methylthio)butan-1-ol (Compound No. 1-46).
References
[1] European Journal of Organic Chemistry, 2008, # 9, p. 1608 - 1614
[2] Angewandte Chemie, 1989, vol. 101, # 2, p. 220 - 222
[3] European Journal of Organic Chemistry, 2004, # 12, p. 2715 - 2722
[4] Journal of Organic Chemistry, 1990, vol. 55, p. 3749 - 3755
[5] Journal of Organic Chemistry, 2008, vol. 73, # 3, p. 1077 - 1087
