Water → HCID 22620189, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-(tert-Butoxycarbonyl)-4-chloro-2-n-pentyl-1,2-dihydropyridine (4.67 g, 16.33 mmol) in 170 ml of THF at −42° C. was added n-butyllithium (7.84 mL, 19.61 mmol) dropwise via syringe. After the mixture had stirred at −42° C. for 1 h, iodomethane (3.1 mL, 48.99 mmol) was added and stirring was continued at −42° C. for 1 h and then at room temperature for 1 h. Water (50 mL) and ether (100 mL) were added, the layers were separated, the aqueous phase was extracted with ether (2×15 mL), and the combined organic extracts were washed with brine. The organic phase was dried over K2CO3 filtered through silica gel/Celite, and concentrated in vacuo to give the crude product. Purification by column chromatography with 5% EtOAc in hexanes afforded 3.6 g (74%) of the product. 1H NMR (250 MHz) d 5.62-5.59 (d, 1 H), 5.31 (br s, 1 H), 4.80-4.72 (q, 1 H), 2.13 (s, 1 H), 1.55-1.26 (m, 17 H), 0.89-0.84 (t, 3 H); 13C NMR (62.7 MHz) 153.0 (s), 136.9 (s), 126.5 (s), 119.3 (s), 112.2 (s), 81.4 (s), 54.1 (s), 31.6 (s), 31.5 (s), 28.1 (s), 24.2 (s), 22.4 (s), 21.9 (s), 13.9 (s), ppm. FT-IR (neat) 2927, 2855, 1706, 1634, 1391, 1128, 1087 cm−1.

Provenance & Evidence