Sodium Chloride → ((1R,4S)-4-Azido-cyclopent-2-enyloxy)-tert-butyl-dimethyl-silane

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared by combining a solution of 630 mg (2.46 mmol) of acetic acid (1S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl ester [synthesized by silylation of commercially available acetic acid (1S,4R)-4-hydroxy-cyclopent-2-enyl ester (Curran, et al. Tetrahedron 1997, 53, 1983-2004)] in 6 mL tetrahydrofuran with a solution of 320 mg (4.91 mmol) of sodium azide in 1.3 mL of water. To this biphasic mixture was added a solution of 112 mg (0.12 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 258 mg (0.98 mmol) of triphenylphosphine in 2 mL tetrahydrofuran, and the reaction mixture was heated to 50° C. for 6 h, when the reaction was complete. Sat. sodium chloride solution was added, and the aqueous phase was repeatedly extracted with ether. The combined organic phase was dried over sodium sulfate, filtered and evaporated. The crude material was purified by silica gel chromatography to yield 475 mg of the title compound (35). 1H NMR (400 MHz, DMSO) δ=0.09 (s, 3H), 0.10 (s, 3H), 0.88 (s, 9H), 1.49 (dt, J=3.9, 14.0 Hz, 1H), 2.69 (dt, J=7.4, 14.1 Hz, 1H), 4.22-4.26 (m, 1H), 4.75-4.79 (m, 1H), 5.92-5.95 (m, 1H), 6.05 (dt, J=1.8, 5.4 Hz, 1H)

Provenance & Evidence