反応 #438344

反応方程式

N-(tert-butoxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

2-imidazolecarboxaldehyde

sodium cyanoborohydride

→

imidazole

収率 28.8%

N-(2-pyridinylmethyl)-N′-(1H-imidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

収率 28.8%

溶媒

MeOH

反応条件

後処理

1. 1
   濃縮The reaction mixture was concentrated in vacuo
2. 2
   その他partitioned between CH2Cl2 (30 mL) and aqueous 1 N sodium hydroxide (30 mL)
3. 3
   洗浄The aqueous layer was washed with CH2Cl2 (2×20 mL)
4. 4
   洗浄the combined organic extracts washed with brine (30 mL)
5. 5
   乾燥dried (MgSO4)
6. 6
   ろ過filtered
7. 7
   濃縮concentrated in vacuo
8. 8
   その他Purification of the crude product by column chromatography on silica gel (CH2Cl2/MeOH, 95:5)

実験手順

To a stirred solution of N-(tert-butoxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (174 mg, 0.38 mmol) in dry MeOH (5 mL) was added 2-imidazolecarboxaldehyde (75 mg, 0.78 mmol) and sodium cyanoborohydride (55 mg, 0.88 mmol) and the mixture was stirred for 40 h. The reaction mixture was concentrated in vacuo and partitioned between CH2Cl2 (30 mL) and aqueous 1 N sodium hydroxide (30 mL). The aqueous layer was washed with CH2Cl2 (2×20 mL) and the combined organic extracts washed with brine (30 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification of the crude product by column chromatography on silica gel (CH2Cl2/MeOH, 95:5) afforded the imidazole derivative (48 mg, 24%) as a clear oil.

出典