HCID 1123811, compound → HCID 59004674, compound

Participants

Reaction Conditions

Reaction Steps

Lithium aluminum hydride (0.263 g, 6.943 mmol) and anhydrous tetrahydrofuran (10 mL) were charged to a dry argon purged flask fitted with magnetic stir bar, condenser and dropping funnel and the mixture cooled to 0° C. A solution of compound 99 (0.70 g, 1.736 mmol) in anhydrous tetrahydrofuran (15 mL) is charged to the dropping funnel and added dropwise to the cold solution over 20 minutes. The resulting mixture was allowed to warm to room temperature over 90 minutes then heated to reflux for 45 minutes. After cooling to room temperature, then to 0° C., the reaction was quenched by the portionwise addition of sodium sulfate decahydrate (approximately 4.0 g). Water (5 mL) and ethylacetate (50 mL) were added and mixture stirred overnight, transferred to a separatory funnel (washing with a small amount of water and ethyl acetate) and the organic layer separated. The aqueous layer was further extracted with ethyl acetate and the combined organic layers washed with brine, dried over sodium sulfate, concentrated and the residue purified via chromatography on silica gel (MeOH:CH2Cl2, 3:97 to 1:9) to yield compound 100 (308 mg, 66.0%) as a pale yellow oil. 1H NMR (DMSO-d6) δ 1.48-1.67 (2×m, 3H), 1.83-1.95 (m, 1H), 2.14 (q, 1H, J=8.6 Hz), 2.28 (s, 3H), 2.32-2.38 (m, 1H), 2.81-2.89 (m, 1H), 2.93-2.99 (m, 1H), 3.10-3.17 (m, 1H), 5.54-5.66 (m, 1H), 6.55 (d, 2H, J=8.9 Hz), 7.17 (d, 2H, J=8.9 Hz); ESI-MS (m/z, %): 269/271 (MH+, 100%).

Provenance & Evidence