تفاعل #612787

معادلة التفاعل

(4S,5R)-tert-butyl 4-(fluoromethyl) -5-(4-iodophenyl)-2,2-dimethyloxazolidine-3-carboxylate

ethynyltrimethylsilane

piperidine

→

title compound

المردود 88.4%

(4S,5R)-tert-butyl 4-(fluoromethyl)-2,2-dimethyl-5-(4-((trimethylsilyl)ethynyl)phenyl)oxazolidine-3-carboxylate

المردود 88.4%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe mixture is filtered through a pad of Celite
2. 2
   غسيلThe pad of Celite is washed with ethylacetate (2×15 ml)
3. 3
   تركيزThe combined organic filtrates were concentrated
4. 4
   أخرىevaporation at reduced pressure
5. 5
   أخرىto give a crude viscous oil
6. 6
   أخرىThe oil is purified by flash column chromatography (grading from 100% hexanes to 15% EtOAc)

الإجراء التجريبي

To a toluene (40 ml) solution of (4S,5R)-tert-butyl 4-(fluoromethyl) -5-(4-iodophenyl)-2,2-dimethyloxazolidine-3-carboxylate (2.0 g, 4.6 mmols) is added ethynyltrimethylsilane (451 mg, 4.6 mmols), copper (I)iodide (88 mg, 0.46 mmols, 0.1 equivs), Bis(triphenylphosphine)palladium(II) dichloride (165 mg, 0.23 mmols, 0.05 equivs) and piperidine (782 mg, 9.2 mmols, 2 equivs). The mixture is heated in an atmosphere of nitrogen at 35° C. for six hours. The mixture is filtered through a pad of Celite. The pad of Celite is washed with ethylacetate (2×15 ml). The combined organic filtrates were concentrated using rotary evaporation at reduced pressure to give a crude viscous oil. The oil is purified by flash column chromatography (grading from 100% hexanes to 15% EtOAc) to give the title compound (1.65 g): m/z (Cl) 306 ([M+H]+−Boc).

المصدر