反应 #1244310

反应方程式

Iodine

Imidazole

tert-butyl (2S)-2-fluoro-3-hydroxypropylcarbamate

Triphenylphosphine

→

tert-butyl (2S)-2-fluoro-3-iodopropylcarbamate

收率 62.0%

溶剂

methylene chloride

methylene chloride

反应条件

后处理

1. 1
   温度cooled to 0° C
2. 2
   其他remained below 10° C
3. 3
   温度to warm to room temperature
4. 4
   workup.STIRRINGstirring
5. 5
   workup.WAITwas continued for 12 h
6. 6
   过滤The reaction mixture was filtered through a pad of Celite®
7. 7
   洗涤washed with additional methylene chloride
8. 8
   浓缩The filtrate was concentrated under reduced pressure
9. 9
   其他purified by silica gel column chromatography
10. 10
    洗涤eluting with methylene chloride

实验过程

Imidazole (19.8 g, 0.29 mol) was dissolved in methylene chloride (900 mL) at room temperature. Iodine (73.9 g, 0.29 mol) was added and the reaction mixture was stirred for 10 min at room temperature and then cooled to 0° C. Triphenylphosphine (76.3 g, 0.29 mol) was added portionwise over 10 min such that the internal temperature remained below 10° C. A solution of tert-butyl (2S)-2-fluoro-3-hydroxypropylcarbamate (45.0 g, 0.23 mol) in methylene chloride (300 mL) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirring was continued for 12 h. The reaction mixture was filtered through a pad of Celite® and washed with additional methylene chloride. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography eluting with methylene chloride. This procedure afforded tert-butyl (2S)-2-fluoro-3-iodopropylcarbamate as a colorless oil (42.5 g, 62%). 1H NMR (300 MHz, CDCl3) δ 4.80-5.10 (br s, 1H), 4.58-4.72 (m, 0.5H), 4.42-4.56 (m, 0.5H), 3.48-3.70 (m, 1H), 3.20-3.46 (m, 3H), 1.48 (s, 9H).

来源