Formaldehyde → HCID 86596682, compound

Participants

Reaction Steps

To 1.08 g (2.9 mmol) of 8-2 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 8-3 as a colorless oil. Data for 8-3: LRMS (ES) calc'd M+H for C13H26N2O3: 259. Found: 259.

Provenance & Evidence