Water → HCID 22620178, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-(tert-Butoxycarbonyl)-4-chloro-2-cyclopentyl-1,2-dihydropyridine (3.69 g, 12.99 mmol) in 180 ml of THF at −42° C. was added n-butyllithium (6.25 mL, 15.59 mmol) dropwise via syringe. After the mixture had stirred at −42° C. for 1 h, iodomethane (2.4 mL, 38.97 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 2.60 g (69%) of the product as an orange oil that was homogeneous by TLC analysis. 1H NMR (250 MHz) δ5.68-5.61 (d, 1 H), 5.37 (br s, 1 H), 4.86-4.73 (q, 1 H), 2.21 (m, 1 H), 2.14 (s, 3 H), 1.76-1.20 (m, 17 H).

Provenance & Evidence