Formaldehyde → HCID 86596682, compound

Participants

Reaction Steps

To 1.08 g (2.9 mmol) of 2-2 in 30 mL of EtOH was added 7 mL (74 mmol) of 1,4-cyclohexadiene and a catalytic amount of 10% Pd on carbon. After stirring overnight, the reaction was filtered through Celite, concentrated by rotary evaporation, and dissolved in 25 mL of MeOH. To this was added 2 mL of AcOH, and 700 μL (8.6 mmol) of 37% aqueous formaldehyde. After stirring overnight, 540 mg (8.6 mmol) of NaCNBH3 in 5 mL of MeOH was added and the reaction was stirred for 1 h more. The solvents were removed by rotary evaporation, the residue was partitioned between EtOAc and aqueous NaHCO3, the organic phase was washed with brine, dried over Na2SO4, and concentrated. The residue was taken up in CH2Cl2, filtered and concentrated to provide 2-3 as a colorless oil. Data for 2-3: LRMS (ES) calc'd M+H for C13H26N2O3: 259. Found: 259.

Provenance & Evidence