Acetone Cyanohydrin → HCID 11602883, compound

Participants

Reaction Steps

To a solution of preparation 20 (58 mg, 0.132 mmol) and triphenyl phosphine (175 mg, 0.67 mmol) and acetone cyanohydrin (0.125 mL, 1.37 mmol) in 1 mL of THF at 0° C. add dropwise via syringe diisopropylazodicarboxylate (0.13 mL, 0.66 mmol). Let the solution warm slowly to room temperature overnight. Concentrate the solution, adsorb the material to silica gel, and purify by silica gel flash chromatography (10 g, 0-30% A/B, A=EtOAc, B=10% CH2Cl2 in hexanes). Dissolve the material in 2 mL of THF and add 1 mL of 5 M aqueous HCl. Stir the solution overnight. Dilute the solution with EtOAc and a little methanol for solubility, wash with saturated aqueous sodium bicarbonate, brine, dry over Na2SO4, filter and concentrate. Adsorb the material to silica gel and purify by silica gel flash chromatography (4 g, 10-60% A/B, A=10% methanol in EtOAc, B=hexanes) to afford example 10. HRMS calc. for C20H17F2NNaO3: 380.1074; found: 380.1060 (M+Na).

Provenance & Evidence