Trifluoroacetic acid → HCID 11756515, compound

Participants

Reaction Steps

Using the same method as for COMPOUND 17 and using INTERMEDIATE 5a (206 mg, 0.44 mmol), 4-(1H-imidazol-1-yl)benzaldehyde (83.6 mg, 0.49 mmol), and decaborane (16.4 mg, 0.13 mmol) afforded COMPOUND 53 (181 mg, 42% yield) as its TFA salt. This material was lyophilized from CH3CN/H2O to produce a colourless solid. Purity (HPLC): >99%; Optical purity (Chiral HPLC): >99%; 1H NMR (400 MHz, CD3OD) δ 1.09 (br t, J=6.7 Hz, 3H), 1.21 (br t, J=6.7 Hz, 3H), 2.63 (br s, 4H), 3.15-3.28 (m, 6H), 3.51 (q, J=6.1 Hz, 2H), 4.32 (s, 1H), 4.43 (s, 2H), 6.47-6.52 (m, 1H), 6.71-6.76 (m, 2H), 7.02 (t, J=8.0 Hz, 1H), 7.26 (d, J=8.2 Hz, 2H), 7.49 (d, J=8.2 Hz, 2H), 7.58 (d, J=8.6 Hz, 2H), 7.64 (d, J=8.6 Hz, 2H), 7.76 (s, 1H), 8.05 (s, 1H), 9.44 (s, 1H). Found: C, 51.44; H, 4.89; N, 9.63. C32H38N6O×1.2 H2O×3.0 CF3COOH has C, 51.49; H, 4.94, N, 9.48%. [α]D17=−2.1 deg [c 0.872, MeOH].

Provenance & Evidence