Water → 4'-(aminomethyl)-2,2-dimethyl-3,4-dihydro-2H,5H-spiro[benzo[h]chromene-6,2'-[1,3]dioxolan]-5-one

Participants

Reaction Steps

To a solution of 4′-(azidomethyl)-2,2-dimethyl-3,4-dihydro-2H,5H-spiro[benzo[h]chromene-6,2′-[1,3]dioxolan]-5-one (0.012 mg, 0.035 mmol) in THF (1.0 mL) is added triphenylphosphine (0.033 mg, 0.13 mmol). The mixture is stirred at room temperature for 3 hour followed by addition of water (50 μL). The reaction is then stirred for another 16 hour at room temperature and solvent is removed under reduce pressure to yield a reside of 4′-(aminomethyl)-2,2-dimethyl-3,4-dihydro-2H,5H-spiro[benzo[h]chromene-6,2′-[1,3]dioxolan]-5-one as confirmed by LC/MS, which indicates the product, which has a molecular weight of 315 Da, is present in the crude residue along with triphenylphosphine oxide (a side product from the triphenylphosphine).

Provenance & Evidence