Ammonium Chloride → HCID 71003680, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1S,3R)-methyl 3-(thiazole-2-carbonyl)cyclopentanecarboxylate (148 mg, 1.75 mmol) in THF (6 mL) and at −78° C. was added methylmagnesium bromide (582 mL, 1.75 mmol), the solution was stirred at −78° C. for 30 minutes. Saturated aqueous ammonium chloride was added and the mixture was allowed to warm to room temperature. The mixture was extracted with EtOAc, organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was absorbed on silica and purified by flash chromatography to afford (1S,3R)-methyl 3-(1-hydroxy-1-(thiazol-2-yl)ethyl)cyclopentanecarboxylate. MS ESI calc'd. for C12H18NO3S [M+H]+ 256. found 256. 1H NMR (500 MHz, DMSO-d6) δ 7.67 (t, J=3.0 Hz, 1H), 7.50 (d, J=3.0 Hz, 1H), 3.58-3.57 (m, 3H), 3.52 (s, 1H), 2.75-2.62 (m, 1H), 2.43-2.35 (m, 1H), 1.97-1.91 (m, 1H), 1.78-1.51 (m, 4H), 1.46-1.44 (m, 3H), 1.25-1.19 (m, 1H).

Provenance & Evidence