Sodium Hydroxide → HCID 59004637, compound

Participants

Reaction Steps

To an ice cold solution of compound 101 (402 mg, 1.052 mmol) in 95% ethanol (20 mL) was added 1M sodium hydroxide (1.052 mL, 1.052 mmol) followed by sodium borohydride (19.9 mg, 0.526 mmol) and the mixture stirred under ice cooling for 45 minutes. The reaction was quenched with ice cold H2O (5 mL), diluted with dichloromethane, transferred to a separatory funnel and the organic layer separated. The aqueous layer was further extracted with dichloromethane (twice) and the combined organic layers washed with brine, dried over sodium sulfate and concentrated to residue. The residue was taken up in anhydrous dioxane (20 mL) and heated to reflux for 2.5 hours. After cooling to room temperature the reaction was treated with ice-cold 2N potassium carbonate, diluted with dichloromethane, transferred to a separatory funnel and the organic layer separated. The aqueous layer was further extracted with dichloromethane (twice) and the combined organic layers washed with water (twice), brine, dried over sodium sulfate concentrated under reduced pressure and the residue purified via chromatography on silica gel (MeOH:CH2Cl2, 3:97) to yield compound 102 (110 mg, 35.7%) as a yellow oil. 1H NMR (DMSO-d6) δ 1.42-1.50 (m, 1H), 1.50-1.60 (m, 2H), 1.62-1.71 (m, 1H), 2.09-2.14 (m, 1H), 2.17 (s, 3H), 2.50-2.57 (m, 1H), 2.90-2.96 (m, 1H), 4.05 (dd, 1H, J=14.1, 6.3 Hz), 4.23 (dd, 1H, J=14.0, 5.1 Hz), 6.41 (d, 1H, J=3.0 Hz), 7.22 (dd, 1H, J=8.9, 1.9 Hz), 7.42-7.49 (m, 2H), 7.71 (d, 1H, J=2.0 Hz); ESI-MS (m/z, %): 293/295 (MH+, 100%).

Provenance & Evidence