Hydrochloric Acid → HCID 78323073, compound

Participants

Reaction Steps

To a solution of NBS (210 mg, 1.3 mmol) in dioxane (4 mL) was added aqueous KHCO3 (260 mg, 2.6 mmol, 4 mL) at room temperature. The mixture was stirred for 30 min at room temperature. Compound 5 (105 mg, 0.26 mmol) in dioxane (10 mL) was added. The reaction was stirred for 14 h at room temperature and then NaBH4 was added (200 mg in 5 portions). The reaction was stirred for 3 h at room temperature. 6 N HCl (10 mL) was added and stirring at room temperature continued for 1 h. The product was extracted into EtOAc (50 mL×2). The combined extracts were dried, filtered, and removed. The residue was purified by flash column chromatography (silica gel eluted with 20% EtOAc in hexanes) to afford compound 6 (62 mg, 56%): mp 157-159° C.; [α]D20 +32.4 (c 0.21, CHCl3); 1H NMR (CDCl3) δ 4.40 (t, J=8.2 Hz, 1H), 4.05-4.10 (m, 1H), 2.56-2.51 (m, 1H), 0.73 (s, 3H); 13C NMR (CDCl3) δ 94.4, 66.3, 47.9, 47.2, 47.0, 45.8, 45.1, 40.4, 38.3, 36.1, 33.9, 33.8, 32.7, 28.4, 25.7, 24.6, 2.32, 12.1; IR νmax 3385, 2212, 1542 cm−1. Anal. Calcd for (C18H29NO3): C, 70.32; H, 9.51; N, 4.56. Found: C, 70.12; H, 9.32; N, 4.33.

Provenance & Evidence