HCID 178418630, compound → HCID 178501141, compound

Participants

Reaction Steps

To a solution of methyl trans-4-(1,3-thiazol-2-ylcarbonyl)cyclohexanecarboxylate (2.59 g, 10.22 mmol) in THF (10 mL) at −78° C. was added cyclopropylmagnesium bromide (0.5 M in THF, 24 mL, 12.00 mmol) and the solution was stirred at this temperature for three hours. The solution was then allowed to warm for 15 minutes and then quenched with aqueous ammonium chloride. The solution was diluted with dichloromethane and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-30% ethyl acetate/hexanes. The product was further purified by reverse phase chromatography (25-100% acetonitrile/water with 0.1% TFA modifier) to afford methyl trans-4-[cyclopropyl(hydroxy)1,3-thiazol-2-ylmethyl]cyclohexanecarboxylate. MS ESI calc'd. for C15H22NO3S [M+H]+ 296. found 296. 1H NMR (500 MHz, CDCl3) δ 7.77 (d, J=3.4 Hz, 1H), 7.37 (d, J=3.4 Hz, 1H), 3.65 (s, 3H), 2.28-2.17 (m, 1H), 2.13-2.02 (m, 3H), 2.01-1.90 (m, 2H), 1.56-1.48 (m, 1H), 1.48-1.39 (m, 1H), 1.39-1.32 (m, 1H), 1.33-1.19 (m, 3H), 0.75-0.62 (m, 1H), 0.61-0.50 (m, 1H), 0.42-0.25 (m, 2H).

Provenance & Evidence