(S)-(-)-1-tert-Butoxycarbonyl-3-aminopyrrolidine

Chemical Properties

Colorless to light yellow liqui

Uses

(S)-(-)-1-Boc-3-aminopyrrolidine may be used to prepare:

• Descarboxamide analog of 4-N-(N^ω-nitro-L-argininyl)-trans-4-amino-L-proline amide.
• Histamine 3 (H₃) receptor antagonists containing pyrrolidin-3-yl-N-methylbenzamide moiety.

Synthesis

To a solution of compound 178 (2.0 g, 9.42 mmol, 1.0 eq.) in methanol (40 mL) was added palladium carbon (1.0 g, 0.94 mmol, 0.1 eq.). The reaction mixture was subjected to hydrogenation at atmospheric pressure and room temperature for 6 hours. After completion of the reaction, the reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure. The target compound (S)-1-Boc-3-aminopyrrolidine was obtained as a yellow oil (1.7 g, 97% yield).

References

[1] Patent: US2009/221565, 2009, A1. Location in patent: Page/Page column 51
[2] Patent: WO2016/34134, 2016, A1. Location in patent: Paragraph 00470
[3] Patent: CN105399698, 2016, A. Location in patent: Paragraph 1340-1342
[4] Patent: WO2005/811, 2005, A1. Location in patent: Page/Page column 61
[5] Patent: WO2005/20975, 2005, A2. Location in patent: Page/Page column 221