反应详情

To a 0° C. solution of spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine] (HCl salt) (1.0 g, 3.6 mmol) in dry acetonitrile (10 mL), under nitrogen, was added NaHCO3 (1.5 g, 18 mmol) followed by dropwise addition of benzyl bromide (560 μL, 4.7 mmol). The cooling bath was removed. Water (25 ml) was then added, and the organic solvent was removed under vacuum. The product was extracted from the aqueous solution with EtOAc (3×150 mL). The organic phases were combined, washed with brine, dried with sodium sulfate, filtered, and concentrated under reduced pressure. The product was purified by column chromatography (silica gel: 5-70% EtOAc in hexanes) to give 1′-benzylspiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine] 660 mg, 55%). ESI-MS m/z calc. 330.4. found 331.5 (M+1)+; Retention time: 1.23 minutes (3 min run).

1. customThe cooling bath was removed
2. additionWater (25 ml) was then added
3. customthe organic solvent was removed under vacuum
4. extractionThe product was extracted from the aqueous solution with EtOAc (3×150 mL)
5. washwashed with brine
6. dry with materialdried with sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe product was purified by column chromatography (silica gel: 5-70% EtOAc in hexanes)