Methanol → HCID 66868945, compound

Participants

Reaction Conditions

Reaction Steps

(±)-(3S*,4S*)-4-Amino-4-(2-fluorophenyl)tetrahydrofuran-3-carboxylic acid (0.22 g) was transferred into the reaction vessel. Methanol (15 mL) was transferred into the reaction vessel. Sulphuric acid (1 mL) was transferred into the reaction vessel. The reaction was stirred at 70° C. for 8 h. The reaction mixture was concentrated under reduced pressure. Saturated sodium bicarbonate (40 mL) was then added followed by an extraction with DCM (3×40 mL). The combined organic phases were dried over MgSO4, filtered and concentrated. The crude product was purified by preparative HPLC (Method B) to give the title compound (120 mg). 1H NMR (400 MHz, CDCl3) δ ppm 3.73 (s, 3H) 3.78 (t, J=8.21 Hz, 1H) 4.02 (dd, J=8.91, 2.97 Hz, 1H) 4.15 (d, J=8.97 Hz, 1H) 4.22 (t, J=8.72 Hz, 1H) 4.36-4.44 (m, 1H) 7.09 (ddd, J=12.41, 8.12, 1.20 Hz, 1H) 7.18 (td, J=7.64, 1.14 Hz, 1H) 7.29-7.35 (m, 1H) 7.63 (td, J=8.05, 1.45 Hz, 1H).

Provenance & Evidence