Journal of Medicinal Chemistry Table 10. continued Article acetonitrile−water in vacuo. The TFA salt was subsequently neutralized by saturated sodium bicarbonate solution and extracted with dichloromethane to get the compound as a free base. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to yield the desired compound 7a-2 (234 mg, 86%). The structure of 7a-2 was veriﬁed by 2-D NMR techniques (Table 10). Synthesis of Compound 7b. To a solution of compound 7a-2 (170 mg, 0.45 mmol) in THF (9 mL) was added 1.0 N BH3·THF (2.70 mL, 2.70 mmol) at rt. The reaction mixture was stirred at reﬂux for 2 h. 4269 dx.doi.org/10.1021/jm300041e | J. Med. Chem. 2012, 55, 4244−4273