Formaldehyde → HCID 11741968, compound

Participants

Reaction Steps

A 28 mL Pyrex-Plus tube containing amine 28 (Example 3, 170 mg, 0.452 mmol) was charged with methanol (2.0 mL), then acetic acid (170 □L), then formaldehyde (110 mg of a 37% aqueous solution, 1.35 mmol), then NaBH3CN (2.26 mL of a 1.0M solution in THF, 2.26 mmol). After stirring at room temperature for 1 hour, the reaction mixture was injected directly onto a 40 g Isco RediSep normal phase silica cartridge, and purified on an Isco OptiX10 CombiFlash instrument using a gradient that started at 100% methylene chloride and ended at 90% methylene chloride, 9% methanol, 1% concentrated arnmonium hydroxide. Fractions containing desired product were pooled and concentrated under reduced pressure, yielding 140 mg of dimethylamine 29. This sample was dissolved in 5 mL methanol and purified on an HPLC column, from 5×1.0 mL injections, using a gradient that started at 40% methanol and 60% water and ended at 100% methanol. Fractions containing desired product were pooled and concentrated under reduced pressure. Yield of 29: 104 mg (57%). 1H NMR (500 MHz, CDCl3) δ 1.39 (s, 6H), 2.15 (s, 6H), 2.54 (s, 2H), 5.11 (bs, 2H), 6.54 (d, J=5.5 Hz, 1H), 7.06 (dd, J=7.3, 2.0 Hz, 1H), 7.13 (m, 2H), 7.67 (m, 3H), 8.12 (d, J=5.5 Hz, 1H), 9.44 (dd, J=7.3, 0.5 Hz, 1H). MS (ESI+) 405.3.

Provenance & Evidence