Ammonia → 6-((tetrahydro-2H-pyran-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-amine

Participants

Reaction Steps

To a solution of 6-((tetrahydro-2H-pyran-2-yl)oxy)tetrahydrofuro[3,2-b]furan-3(2H)-one (3.5 g, 15.3 mmol) in a solution of NH3 in MeOH (30 mL, 7 M) was added titanium isopropoxide (10.9 g, 38.3 mmol) at rt, and then the mixture was stirred at rt overnight. To the reaction mixture was added NaBH4 (1.16 g, 30.6 mmol) slowly at rt, and the mixture was stirred at rt for another 10 h and then quenched with H2O (50 mL). The resulting mixture was filtered and washed with EtOAc (50 mL). The filtrate was extracted with EtOAc (80 mL×3), and then the combined organic phases were washed with brine (200 mL), dried over anhydrous Na2SO4, then filtered and concentrated in vacuo to give product as crude oil (3.6 g, crude product).

Provenance & Evidence