Propanal → HCID 10345099, compound

Participants

Reaction Steps

Using the same method as for COMPOUND 61 and using COMPOUND 60 (86.0 mg, 0.20 mmol), propionaldehyde (0.014 mL, 0.19 mmol) and decaborane (7.2 mg, 0.059 mmol) afforded COMPOUND 62 (89 mg, 55% yield) as its TFA salt. This material was lyophilized from CH3CN/H2O to produce a hygroscopic, slightly yellow solid. Purity (HPLC): >97%; Optical purity (Chiral HPLC): >93%; 1H NMR (400 MHz, CD3OD) δ 1.01 (t, J=7.4 Hz, 3H), 1.09 (br t, J=6.6 Hz, 3H), 1.22 (br t, J=6.6 Hz, 3H), 1.70 (sextet, J=7.6 Hz, 2H), 1.95-2.04 (m, 2H), 2.39 (br s, 2H), 3.01 (br s, 2H), 3.15-3.28 (m, 8H), 3.33 (s, 3H), 3.45-3.61 (m, 6H), 4.55 (s, 1H), 7.10-7.16 (m, 1H), 7.34 (d, J=8.2 Hz, 2H), 7.37-7.44 (m, 3H), 7.57 (d, J=8.0 Hz, 2H). Found: C, 53.22; H, 6.76; N, 7.48. C29H44N4O2×2.0 H2O×2.0 CF3COOH has C, 53.22; H, 6.77; N, 7.52%. [α]D17=−1.5 deg [c 0.779, MeOH].

Provenance & Evidence