Hydrochloric Acid → 1,2,7,8,9,10,11,11a-octahydro-6bH-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole

Participants

Reaction Conditions

Reaction Steps

Tert-butyl 1,7,8,10,11,11b-hexahydropyrano[4′,3′,2′:3,4]indeno[1,2-d]azepine-9(2H)-carboxylate (407 mg, 1.24 mmol) was dissolved in TFA (10 mL). This solution was cooled to 0° C., and NaCNBH3 (234 mg, 3.72 mmol) was added in small portions. The reaction was stirred at 0° C. for 1 hr. Conc. HCl (5 mL) was added to the reaction flask, and then the mixture was refluxed at 50° C. for 30 min. The reaction was re-cooled to 0° C., and ice chips were added. The solution was basified with 50% NaOH until a pH=14. The reaction was extracted with CHCl3 (3×20 mL). The combined organic layers were washed with brine, dried, and concentrated to afford the title compound (321 mg, 100%) as an amorphous solid. 1H NMR (CDCl3, 300 MHz) δ6.57-6.67 (3H, m), 4.39-4.43 (2H, m), 3.61-3.69 (1H, m), 3.45 (1H, dt, J=3.3 Hz, 9.2 Hz), 3.00-3.24 (3H, m), 2.69-2.89 (3H, m), 2.02-2.16 (2H, m), 1.83-1.97 (2H, m).

Provenance & Evidence