Triphenylphosphine → Tert-butyl 2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-phenylmorpholine-4-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 4-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxy-2-phenylbutyl(2-hydroxyethyl)carbamate (770 mg, 1.7 mmol) and triphenylphosphine (551 mg, 2.1 mmol) in 8 mL toluene was added diethyl azodicarboxylate (0.96 mL of a 40% solution in toluene, 2.1 mmol) and the reaction was stirred for 24 h. After evaporation, the residue was chromatographed (10% EtOAc/hex) to afford tert-butyl 2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-phenylmorpholine-4-carboxylate as an oil, which was used without further purification. ESI-MS 422 (M+H).

Provenance & Evidence