Triphenylphosphine → HCID 19017868, compound

Participants

Reaction Steps

To a stirred solution of cycloheptanemethanol (11.2 g, 100 mmol), tert-butyl N-(tert-butoxycarbonyloxy)carbamate (7.2 g, 104 mmol) and triphenylphosphine (7.2 g, 104 mmol) in THF (150 mL) was added diethylazodicarboxylate dropwise. The mildly exothermic reaction was stirred 3 hours, then concentrated in vacuo. The concentrate was treated with hexane, and the crystalline by-product was vacuum filtered. The filtrate was concentrated in vacuo and the resulting residue was chromatographed (silica gel, ethyl acetate:hexanes, 2:8) to afford the protected hydroxylamine derivative.

Provenance & Evidence