Reaction #155381

Reaction equation

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

Solvents

acetone

Conditions

Workup

1. 1
   OtherTo a 50-mL round-bottom flask equipped with a magnetic stirbar
2. 2
   Otherthe reaction mixture was capped with a rubber septum
3. 3
   OtherThe sodium chloride side product was remove by gravity filtration
4. 4
   Concentrationthe filtrate was concentrated on a rotary evaporator
5. 5
   OtherThe crude oily product was purified by flash chromatography
6. 6
   Washeluting with hexanes

Procedure

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).

Source