Formaldehyde → N-benzyl-6-(benzyloxy)-N-methylhexahydrofuro[3,2-b]furan-3-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of N-benzyl-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-amine (9.88 g, 30.36 mmol) in HCOOH (19 mL) was added formalin (2.96 g, 36.43 mmol). After addition, the reaction mixture was stirred at 110° C. overnight and concentrated in vacuo. The residue was adjusted to pH=8 with a saturated Na2CO3 solution and extracted with EtOAc (100 mL×3). The combined organic phases were washed with water (100 mL×3) followed by brine (100 mL), then dried over anhydrous Na2SO4, then filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/2) to give the title compound as yellow oil (4.77 g, 46.4%).

Provenance & Evidence