反应详情

To a stirring solution of cis-(3-hydroxy-cyclopentyl)-carbamic acid tert-butyl ester (850 mg, 4.22 mmol) and triphenylphosphine (1.53 g, 5.83 mmol) in THF (25 mL) cooled to 2° C. was added DEAD reagent (0.92 mL, 5.84 mol) over 5 minutes. The mixture was stirred for 5 minutes and DPPA (1.26 mL, 5.84 mmol) was added over 5 minutes. Stirring was continued for 17 hours at room temperature. The mixture was evaporated to dryness. The residue was stirred in ethyl ether briefly and the white solid triphenylphosphine oxide was removed by filtration (1 g). The filtrate was again reduced in volume and purified by silica gel chromatography eluting with ethyl acetate and hexanes to afford trans-(3-azido-cyclopentyl)-carbamic acid tert-butyl ester (950 mg).

1. stirringStirring
2. waitwas continued for 17 hours at room temperature
3. customThe mixture was evaporated to dryness
4. stirringThe residue was stirred in ethyl ether briefly
5. customthe white solid triphenylphosphine oxide was removed by filtration (1 g)
6. custompurified by silica gel chromatography
7. washeluting with ethyl acetate and hexanes