Hydrochloric Acid → HCID 13042967, compound

Participants

Reaction Steps

To a stirred solution of the epoxide (177 mg, 1 mmol, Example 303) in tetrahydrofuran (8 mL), lithium bromide (543 mg, 6.25 mmol, Aldrich) and copper(II)bromide (725 mg, 3.25 mmol, Aldrich) were added and the mixture was stirred at room temperature overnight. The mixture was poured into 0.1N hydrochloric acid (33 mL) and extracted with ethyl acetate (3×10 mL). The extracts were combined, washed with water, brine and dried with MgSO4. The solvent was removed to give the desired product as colorless oil after passing through an aluminum column (eluted with 5% methanol/dichloromethane). 237 mg, 92%. H1NMR (300 MHz, CDCl3), ppm: 2.00–2.20 (m), 1H; 2.38–2.52 (m), 1H; 2.70 (br), 1H (OH); 2.99 (s), 3H; 3.0–3.20 (m), 2H; 3.50–3.51 (m), 1H; 3.80–3.97 (m), 2H; 4.0–4.10 (m), 1H. The compound was used directly for the next step.

Provenance & Evidence