Acetic Acid → HCID 22041386, compound

Participants

Reaction Steps

To a solution of 2-amino-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (70.10 g, 0.345 mol) and formaldehyde (280 mL, 10 eq) in 2 L of acetonitrile cooled to 0° C. was added sodium cyanoborohydride (65 g, 3 eq.) in portions while maintaining the temperature between 10–20° C. Glacial acetic acid was added to adjust the pH to 7. The reaction was stirred for 2 hrs at room temperature and the resulting mixture was partitioned between 1N NaOH and EtOAc, the organic phase was washed with water and brine, dried over sodium sulfate, filtered and evaporated. Chromatography on silica gel (hexanes/EtOAc 95:5) gave 54.90 g (70%, 2 steps) of 2-dimethylamino-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene. 1H-NMR (300 MHz, CDCl3): 1.25 (s, 6 H), 1.29 (s, 6 H), 1.66 (s, 4 H), 2.91 (s, 6 H), 6.62 (dd, J=3.0 Hz, J=8.7 Hz, 1 H), 6.67 (d, J=2.7 Hz, 1 H), 7.19 (d, J=8.7 Hz, 1 H).

Provenance & Evidence