反応 #53234

反応方程式

DBU

N-(tert-butyloxycarbonyl)hydroxylamine

6-bromohexan-1-ol

→

compound 27

収率 77.2%

6(tert-butyloxycarbonylaminooxy)hexan-1-ol

収率 77.2%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   濃縮The mixture was concentrated
2. 2
   その他to give a yellow oil
3. 3
   その他Purification by silica gel chromatography (35/5/65 EtOAc/MeOH/hexanes)

実験手順

To a solution of 179 μL (183 mg, 1.2 mmol) of DBU in 1 mL of CH2Cl2 was added 133 mg (1.0 mmol) of N-(tert-butyloxycarbonyl)hydroxylamine (Aldrich Chemical Co.) and 157 μL (217 mg, 1.2 mmol) of 6-bromohexan-1-ol (Aldrich Chemical Co.), and the mixture was stirred for 18 hours at room temperature. The mixture was concentrated to give a yellow oil. Purification by silica gel chromatography (35/5/65 EtOAc/MeOH/hexanes) gave 180 mg (77%) of compound 27 as a colorless oil: 1H NMR (CDCl3) δ 1.39 (m, 4H), 1.48 (s, 9H), 1.59 (m, 4H), 3.63 (t, 2H), 3.85 (t, 2H), 7.42 (s, 1H); 13C NMR (CDCl3) δ 25.6, 25.8, 28.1, 28.4, 62.8, 76.8, 81.7, 157.2.

出典