Facile scalable reduction of N-acylated dihydropyrazoles

作者：Curtis Michael D^*; Hayes Nancy C; Matson Patricia A

来源：Journal of Organic Chemistry, 2006, 71(13): 5035-5038.

DOI：10.1021/jo060567j

The reduction of a variety of highly functionalized N-acylated dihydropyrazoles (1) with BH3, pyridine is described. The process through which this unexpectedly difficult reduction was discovered and developed is reported. A facile atom-efficient route to the N-acylated dihydropyrazole reduction precursors (1) is also illustrated. The resulting acylpyrazolidine products (2) that arise upon reduction were isolated in good to high yields following exposure to reaction conditions which have been shown to tolerate a variety of different functional groups. Finally, this route has been demonstrated on a kilogram scale and provides direct access to potential proline surrogates for peptidomimetic applications.

• 出版日期2006-6-23