Triphenylphosphine → tert-butyl 2-[(2,2-dioxido-3-phenyl-2,1,3-benzothiadiazol-1(3H)-yl)methyl]morpholine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (prepared analogously as in general procedure I, 246 mg, 1.00 mmol), tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (228 mg, 1.05 mmol, 1.05 equiv.) and triphenylphosphine (289 mg, 1.10 mmol, 1.1 equiv.) in tetrahydrofuran (5 mL) was cooled to 0° C. in an ice bath. Diispropyl azodicarboxylate (0.22 mL, 1.1 mmol, 1.1 equiv.) was added dropwise via a syringe. The reaction mixture was stirred overnight while warming to room temperature. Solvent was removed under reduced pressure and the residue was purified by Isco flash column chromatography (silica gel, 3-30% ethyl acetate/hexane) to give 398 mg (89%) of tert-butyl 2-[(2,2-dioxido-3-phenyl-2,1,3-benzothiadiazol-1(3H)-yl)methyl]morpholine-4-carboxylate as a white foam. MS (ESI) m/z 445.9 ([M+H]+).

Provenance & Evidence