反応 #155381

反応方程式

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

溶媒

acetone

反応条件

後処理

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

実験手順

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).

出典