Simple Preparation of N-Protected Chiral β-Amino Alkyl Thiols from Corresponding Iodides Employing Sodium Trithiocarbonate

Abstract

A simple protocol for the preparation of N-protected amino alkyl thiols is reported that employs a reaction of sodium trithiocarbonate (Na₂CS₃) with N-protected amino alkyl iodides. Na₂CS₃ is easy to prepare and the protocol circumvents the use of strong bases and multiple steps. All the thiol compounds made were obtained as enantiopure samples and were characterized employing NMR and mass spectrometry.

GRAPHICAL ABSTRACT

Keywords:

• Alkyl iodide
• chiral β-amino alkyl thiol
• sodium trithiocarbonate

ACKNOWLEDGMENTS

The authors thank the University Grants Commission, New Delhi (UGC), for financial support [F. No. 37-79/2009 (SR)]. The departments of Inorganic and Physical Chemistry (IPC) and Organic Chemistry at IISc, Bangalore, are thanked for the compound characterization data. Timely help from H. N. Gopi, IISER, Pune, during the preparation of the manuscript is gratefully acknowledged.

Notes

^a [M + K]⁺.