Novel route for the synthesis of 8-oxa-3-azabicyclo[3.2.1]octane: One-pot aminocyclization of 2,5-tetrahydrofurandimethanol catalyzed by Pt/NiCuAlOx

• 8-oxa-3-azabicyclo[3.2.1]octane was synthesized from THDMF.
• Pt/NiCuAlOx is an active catalyst for aminocyclization of THDMF.
• The one-pot synthesis of 8-oxa-3-azabicyclo[3.2.1]octane was realized.

2,5-Tetrahydrofurandimethanol (THFDM) was selectively transformed into 8-oxa-3-azabicyclo[3.2.1] octane (OABCO), a valuable building block for the synthesis of bioactive molecules, via one-pot aminocyclization with ammonia catalyzed by Pt/NiCuAlOx. Under optimized conditions (200 °C, 6–16 h, 0.5 MPa hydrogen, 0.4 MPa ammonia), the OABCO yield reached 58% with 100% THFDM conversion.

Figure optionsDownload as PowerPoint slide