Sodium Hydroxide → HCID 59004638, compound

Participants

Reaction Steps

To an ice cold solution of compound 79 (583 mg, 1.526 mmol) in 95% ethanol (25 mL) was added 1M sodium hydroxide (1.526 mL, 1.526 mmol) followed by sodium borohydride (28.9 mg, 0.763 mmol) and the mixture stirred under ice cooling for 45 minutes. The reaction was quenched with ice cold H2O (25 mL), diluted with CH2Cl2, transferred to a separatory funnel and the organic layer separated. The aqueous layer was further extracted with CH2Cl2 (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 (25 mL) and heated to reflux for 3 hours. After cooling to room temperature the reaction was treated with ice-cold 2N potassium carbonate, diluted with CH2Cl2, transferred to a separatory funnel and the organic layer separated. The aqueous layer was further extracted with CH2Cl2 (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 (2M NH3 in methanol:CH2Cl2 2.5:97.5 to 5:95) to yield an off white solid, 80 (265 mg, 59.3%). 1H NMR (DMSO-d6) δ 1.83-1.93 (m, 2H), 1.95-2.04 (m, 2H), 2.13 (dt, 2H, J=11.5, 2.2 Hz), 2.23 (s, 3H), 2.89 (d, 2H, J=11.4 Hz), 4.28-4.35 (m, 1H), 6.44 (d, 1H, J=3.1 Hz), 7.22 (dd, 1H, J=8.7, 1.8 Hz), 7.51-7.56 (m, 2H), 7.72 (d, 1H, J=1.9 Hz); ESI-MS (m/z, %): 293/295 (MH+, 100%).

Provenance & Evidence