Hydrochloric Acid → HCID 57986952, compound

Participants

Reaction Steps

Under N2, to a solution of crude of 11 (1 mmol) in dried MeOH (5 mL) was added dropwise conc.HCl (2 mL) over 1 hr then stirred for overnight. After concentration, the residue was basified with NaHCO3 at 0° C. The mixture was extracted with CH2Cl2 (5×20 mL). The combined extraction were dried over MgSO4, filtered and concentrated. The crude was submitted to silica gel column chromatography (CH2Cl2:MeOH:NH4OH=500:9:1-100:9:1) to give 12 (95%, from 10). [α]D−3.6 (c 1.45, CHCl3); 1H NMR (CDCl3, 400 MHz) δ 2.75 (d, J=13 Hz, 1H), 3.05 (d, J=13 Hz, 1H), 3.56 (d, J=10 Hz, 1H), 3.73 (s, 3H), 3.87 (d, J=10 Hz, 1H), 7.02 (m, 1H), 7.13 (m, 1H), 7.22-7.27 (m, 2H). 13C NMR (CDCl3, 75 MHz) δ 41.5, 52.4, 63.6, 67.7, 127.4, 128.0, 129.8, 129.9, 134.3, 137.5, 175.3; IR (film): 3359, 3300, 3180, 1736, 1083 cm−1; Mass (ESI) 244.02 ([MH]+).

Provenance & Evidence