Sodium Bicarbonate → HCID 21072012, compound

Participants

Reaction Conditions

Reaction Steps

The crude product from step 3 (7.0 g) was dissolved in MeOH (100 mL) and the solution was diluted with 6N HCl (100 mL). The resulting brown solution was stirred and heated in an oil bath at 80° C. for one hour. After cooling, the mixture was diluted with EtOAc (300 mL), stirred, and neutralized by the careful addition of aqueous 5% NaHCO3 and solid NaHCO3. The layers were separated and the aqueous portion was extracted with EtOAc (100 mL). The combined organics were washed with water and brine, dried over MgSO4, filtered, and concentrated under vacuum to an orange-red solid. The crude product was purified by Biotage flash chromatography on a 75 L silica gel column (7.5×35 cm), eluting with 2:1 hexane-EtOAc. The product-containing fractions were evaporated under vacuum to an orange solid (4.2 g) which was shown by 1H NMR to contain 7-amino-9a-butyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one along with approximately 10% of the 9a-butyl-4-methyl-8,9,9a,10-tetrahydro-7H-indenol[1,2-g]quinolin-7-one by-product. This material was used in the next step without further purification.

Provenance & Evidence