Hydrochloric Acid → HCID 90388527, compound

Participants

Reaction Steps

To a solution of compound 50 (250 mg containing the aromatic impurity carried over from compound 48) in methanol (30 mL) was added 6 N HCl (15 mL) at room temperature. After 4 h, the product was extracted into dichloromethane (50 mL×3), and 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 give compound 51 (84 mg): mp. 163-165° C.; [α]D25 −33.9 (c 0.18, CHCl3); 1H NMR (CDCl3) δ 4.06-4.00 (m, 1H), 0.88 (s, 3H); 13C NMR (CDCl3) δ 121.4, 66.2, 48.4, 48.0, 47.0, 45.0, 44.2, 40.3, 39.8, 38.1, 36.0, 33.9, 33.8, 32.7, 28.4, 26.4 (2×C), 23.2, 14.2; IR νmax 3456, 2235 cm−1. Anal. Calcd for (C19H29NO): C, 79.39; H, 10.17. Found: C, 79.16; H, 10.14.

Provenance & Evidence