Triphenylphosphine → HCID 22107091, compound

Participants

Reaction Steps

A mixture of the compound prepared as described in Example 4 (318 mg), triphenylphosphine (577 mg), and tetrazole (155 mg) in dry tetrahydrofuran (4.5 ml) was cooled in an ice/water bath, and treated with diethyl azodicarboxylate (383 mg) over a ten minute period. After the addition was complete, the reaction was allowed to warm to room temperature. After about 171/2 hours, the reaction solution was concentrated in vacuo to give a greasy crystalline mass. This material was diluted with chloroform (10 ml) and concentrated in vacuo. This procedure was repeated to remove traces of tetrahydrofuran. The residue was dissolved in chloroform (10 ml) and purified by centrifugal thin-layer chromatography, eluting with ethyl acetate/hexane (1:1) followed by ethyl acetate/hexane (9:1), ethyl acetate, ethyl acetate/methanol (9:1), and ethyl acetate/methanol (4:1). The first isomer to elute was the tetrazol-2-yl compound, and the second isomer to elute was the tetrazol-1-yl compound. Fractions containing each of these isomers in pure form were pooled and concentrated in vacuo. The residue was triturated in methylene chloride (3 ml), and the title compounds isolated by filtration to give 46 mg of the tetrazol-2-yl compound and 227 mg of the tetrazol-1-yl compound.

Provenance & Evidence