反应 #155381

反应方程式

chloromethyl alkoxyamine

N-tert-Butyl-O-[1-(4-chloromethyl-phenyl)-ethyl]-N-(2-methyl-1-phenyl-propyl)-hydroxylamine

sodium iodide

→

iodomethyl

N-tert-Butyl-O-[1-(4-iodomethyl-phenyl)-ethyl]-N-(2-methyl-1-phenyl-propyl)-hydroxylamine

溶剂

acetone

反应条件

后处理

1. 1
   其他To a 50-mL round-bottom flask equipped with a magnetic stirbar
2. 2
   其他the reaction mixture was capped with a rubber septum
3. 3
   其他The sodium chloride side product was remove by gravity filtration
4. 4
   浓缩the filtrate was concentrated on a rotary evaporator
5. 5
   其他The crude oily product was purified by flash chromatography
6. 6
   洗涤eluting with hexanes

实验过程

To a 50-mL round-bottom flask equipped with a magnetic stirbar was added chloromethyl alkoxyamine 3 (1.789 g, 4.784 mmol) and acetone (20 mL). To the resulting solution was added sodium iodide (2.869 g, 19.14 mmol, 4 equiv) and the reaction mixture was capped with a rubber septum and allowed to stir for 24 hours at room temperature. The sodium chloride side product was remove by gravity filtration, and the filtrate was concentrated on a rotary evaporator. The crude oily product was purified by flash chromatography, eluting with hexanes. The desired iodomethyl akoxyamine 4 was obtained as a colorless oil (1.968 g, 88.3% yield). ESI-MS: m/z=466.0, observed; 465.41, calculated. 1H NMR (500 MHz, CDCl3, both diastereomers) δ 7.5-7.1 (m, 18H), 5.35 (t, 2H) 4.90 (q+q, 2H, both diastereomers), 4.55 (s, 4H), 3.55 (m, 2H), 3.40 (d, 1H, minor diastereomer), 3.30 (d, 1H, major diastereomer), 2.40 (m, 2H, both diastereomer), 2.30 (d, 2H), 1.65 (d, 3H, minor diastereomer), 1.58 (d, 3H, major diastereomer), 1.33 (d, 3H, minor diastereomer), 1.05 (s, 9H, major diastereomer), 0.98 (s, 6H), 0.95 (d, 3H, major diastereomer), 0.89 (d, 12H), 0.85 (d, 6H), 0.82 (s, 9H, minor diastereomer), 0.68 (s, 2H), 0.59 (d, 3H, minor diastereomer), 0.28 (d, 3H, major diastereomer).

来源