Borane;tetrahydrofuran → 7,10-Diazatetracyclo[8.5.1.05,16.011,15]hexadeca-1,3,5(16)-triene

Participants

Reaction Steps

To a solution of 3,4,9,10-tetrahydro-8H-cyclopenta[b][1,4]diazepino[6,7,1-hi]indole (61 mg, 0.29 mmol) in TFA (2 mL) being cooled in an ice-bath, BH3.THF (0.7 mL, 0.7 mmol, 1 M THF) was added slowly under Ar. After 4 h, the reaction mixture was concentrated in vacuo then CHCl3 (3 mL) and 1 N HCl (3 mL) were added. The mixture was stirred for 1 h before separating the two layers. The aqueous layer was basified to pH 13-14 with 5 N NaOH then extracted with CHCl3 (3×3 mL). The combined organic layers was dried over Na2SO4, filtered and concentrated in vacuo to give 36 mg (58%) of the title compound as a thin white film.

Provenance & Evidence