Hydrochloric Acid → HCID 78323391, compound

Participants

Reaction Steps

To compound 9 (165 mg, 0.5 mmol) in methanol (9 mL) and dichloromethane (3 mL) was added 6 N HCl (10 ml) at room temperature. After 14 h, the product was extracted into EtOAc (50 mL×2). The combined extracts were dried, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel eluted with 25% EtOAc in hexanes) to afford compound 10 (135 mg, 94%): mp 162-164° C.; [α]D20 +33.9 (c 0.31, CHCl3); 1H NMR (CDCl3) δ 4.06 (s, br, 1H), 0.86 (s, 3H); 13C NMR (CDCl3) δ 121.3, 66.1, 48.3, 47.9, 46.9, 44.9, 44.2, 40.2, 39.8, 38.1, 36.0, 33.8, 33.7, 32.6, 28.4, 26.3 (2C), 23.1, 14.2; IR νmax 3456, 2235, 1447 cm−1. Anal. Calcd for (C19H29NO): C, 79.39; H, 10.17; N, 4.87. Found: C, 79.60; H, 10.26; N, 4.92.

Provenance & Evidence