Benzylamine → trans-4-(Benzylamino)tetrahydrofuran-3-ol

Ti(OiPr)4 (1.0 mL, 3.48 mmol) was added to a solution of 3,6-dioxabicyclo[3.1.0]hexane (1.5 g, 17.4 mmol) in benzylamine (2.0 mL). The mixture was irradiated in a microwave reactor at 130° C. for 2 hours. It was cooled to room temperature, and 50 mL of saturated aqueous NH4Cl solution and 20 mL of EtOAc were added to the reaction. The mixture was stirred for 10 minutes. The resulting gummy precipitate was filtered over a celite bed, and the filtrate was extracted using EtOAc (100 mL). The organic layer was separated, washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by reverse phase chromatography on a C-18 column (0-100% CH3CN/water) to afford trans-4-(benzylamino) tetrahydrofuran-3-ol. MS APCl calc'd for C11H15NO2 [M+H]+ 194. found 194.

1. customThe mixture was irradiated in a microwave reactor at 130° C. for 2 hours
2. filtrationThe resulting gummy precipitate was filtered over a celite bed
3. extractionthe filtrate was extracted
4. customThe organic layer was separated
5. washwashed with brine
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was purified by reverse phase chromatography on a C-18 column (0-100% CH3CN/water)

ORD-Eintrag

ord-5b84ec78922c42d49a739441b7ccf017

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08846657B2