Triphenylphosphine → HCID 131733885, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 17D (640 mg, 2.131 mmol), (R)-tetrahydrofuran-3-ol (413 mg, 4.69 mmol) and triphenylphosphine in THF (5 mL) at 0° C., was added diisopropyl azodicarboxylate (0.930 mL, 4.69 mmol) dropwise. The reaction mixture was stirred 0° C. for 30 min, and at rt for 16 h. The mixture was concentrated and purified by flash chromatography (0-50% EtOAc in hexanes). The desired fractions were combined, concentrated. The residue was dissolved in MeOH (10 mL) and THF (2 mL). To this solution was added ammonium chloride (2.250 mL, 63.9 mmol) and zinc (0.195 mL, 21.31 mmol). The mixture was stirred at rt for 2 h, concentrated, stirred with sat. Na2CO3 (50 mL) for 20 min, extracted with EtOAc (3×20 mL). The residue was purified by flash chromatography. The desired fractions were concentrated, dissolved in EtOAc (5 mL), and treated with HCl (4N, 5 mL) for 3 h at rt. The mixture was concentrated to give 39A (630 mg, 2.012 mmol, 94% yield) as a yellow solid. MS (ESI) m/z: 242.2 (M+H)+.

Provenance & Evidence