Sodium Bicarbonate → HCID 86605480, compound

Participants

Reaction Conditions

Reaction Steps

1.0 g of 6-hydroxy-5,7-dimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one oxime was dissolved in 20 mL of THF and cooled to 0° C. under nitrogen. 3 mL of (8M) borane-pyridine complex was added via syringe followed by 12 mL of (4 M) HCl-dioxane via a syringe pump over 45 min. After complete addition, the ice bath was removed and the reaction slowly warmed to room temperature then stirred overnight. The next day, the solution was added to sat. NaHCO3, extracted with EtOAc, washed with additional sat. NaHCO3, brine and dried over Na2SO4. The crude material was purified on a silica column eluting with 1:8 EtOAc/Hexanes to yield 699 mg of 4-(hydroxyamino)-5,7-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol.

Provenance & Evidence