Synthesis
The general procedure for the synthesis of (S)-(-)-3-chloro-1-phenyl-1-propanol from 3-chloropropiophenone was as follows: 3.36 g (40.0 mmol) of potassium formate (HCOOK) was used as a hydrogen source under argon protection, 2.609 mg (4.0 μmol) of Cp*IrCl[(S,S)-MsDPEN] was used as a catalyst, and 1.349 g (8.0 mmol) β-chloropropiophenone in a 20 mL Schlenk tube. 2 mL of water and 2 mL of toluene were added to the reaction system and the resulting mixture was stirred at 50 °C for 24 hours. Upon completion of the reaction, the organic phase was washed three times with 3 mL of water, followed by distillation under reduced pressure to remove toluene to give optically active (S)-(-)-3-chloro-1-phenyl-1-propanol. The optical purity of the product was confirmed by GC analysis to be 85% ee in 94% yield.
References
[1] Patent: US2009/62573, 2009, A1. Location in patent: Page/Page column 7; 14
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 6, p. 1009 - 1017
[3] Patent: KR2015/116956, 2015, A. Location in patent: Paragraph 0176-0179
[4] Patent: KR2016/44117, 2016, A. Location in patent: Paragraph 0063-0066
[5] Organic and Biomolecular Chemistry, 2011, vol. 9, # 10, p. 3854 - 3862
