반응 #48683

반응 방정식

ethyl acetate

N-iodosuccinimide

((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester

2,2-dimethyl-1-vinyloxypropane

→

desired compound

수율 84.2%

{(S)-2-benzyloxy-1-[1-(2,2-dimethylpropoxy)-2-iodoethoxymethyl]-ethyl}-carbamic acid tert-butyl ester

수율 84.2%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도Cool to room temperature
2. 2
   세척Wash with water and saturated aqueous sodium chloride
3. 3
   건조Dry (magnesium sulfate)
4. 4
   여과filter
5. 5
   농축concentrate
6. 6
   기타purify
7. 7
   세척(silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)

실험 절차

Add N-iodosuccinimide (14.19 g, 74.63 mmol) to ((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester (15.00 g, 53.30 mmol) and 2,2-dimethyl-1-vinyloxypropane (9.13 g, 79.96 mmol) in acetonitrile (267 mL) at room temperature. Heat to 60° C. under nitrogen for 2 hours. Cool to room temperature and dilute with ethyl acetate. Wash with water and saturated aqueous sodium chloride. Dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes) to give the desired compound as an oil (23.4 g 84.2%).

출처