反応 #791667

反応方程式

sodium hydride

( A )

O-Benzyl-N-(tert-butoxycarbonyl)hydroxylamine

EtOAc CHCl3

5-chlorovaleronitrile

→

( B )

収率 87.0%

O-Benzyl-N-(tert-butoxycarbonyl)-N-(4-cyanobutyl)-hydroxylamine

収率 87.0%

溶媒

DMF

反応条件

後処理

1. 1
   温度the suspension heated at 80°-85° C. for 4 h under argon
2. 2
   温度After cooling
3. 3
   その他the reaction was quenched with H2O (100 mL)
4. 4
   抽出extracted with ether (4×75 mL)
5. 5
   洗浄The combined organic layers were washed with 100 mL each of 1% aqueous Na2SO3, H2O and brine
6. 6
   濃縮concentrated
7. 7
   その他to give 4.39 g crude product

実験手順

Sodium iodide (84 mg, 0.56 mmol) and then sodium hydride (80% oil dispersion, 0.49 g, 16.3 mmol) were added to (A) (2.68 g, 12.0 mmol) in dry DMF (40 mL). After stirring 15 min, 5-chlorovaleronitrile (1.5 mL, 13.3 mmol) was added, and the suspension heated at 80°-85° C. for 4 h under argon. After cooling, the reaction was quenched with H2O (100 mL), then extracted with ether (4×75 mL). The combined organic layers were washed with 100 mL each of 1% aqueous Na2SO3, H2O and brine and then concentrated to give 4.39 g crude product. Column chromatography with 4.5% EtOAc/CHCl3 produced 3.17 g of (B) (87% yield): NMR δ 1.5-1.75 (s+m, 13 H), 2.3 (t, 2 H), 3.4 (t, 2 H), 4.77 (s, 2 H), 7.3 (s, 5 H). Anal. Calcd for C17H24N2O3 : C, 67.08; H, 7.95; N, 9.20. Found: C, 67.19; H, 7.99; N, 9.11.

出典