反応 #438356

反応方程式

di-t-butyldicarbonate

sodium borohydride

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

2-imidazolecarboxaldehyde

→

desired product

収率 40.1%

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

収率 40.1%

溶媒

MeOH

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred for 40 min
2. 2
   濃縮The reaction mixture was concentrated in vacuo
3. 3
   その他partitioned between CH2Cl2 (25 mL) and saturated aqueous sodium bicarbonate (25 mL)
4. 4
   洗浄The aqueous layer was washed with CH2Cl2 (2×20 mL)
5. 5
   乾燥the combined organic phases were dried (Na2SO4)
6. 6
   ろ過filtered
7. 7
   濃縮concentrated in vacuo
8. 8
   workup.DISSOLUTIONThe crude amine was dissolved in THF (10 mL)
9. 9
   その他Purification of the crude material by column chromatography on silica gel (CH2Cl2/MeOH, 96:4 followed by 9:1)

実験手順

To a stirred solution of N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-(2-aminoethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (333 mg, 0.57 mmol) in dry MeOH (5 mL) was added 2-imidazolecarboxaldehyde (110 mg, 1.14 mmol) and the mixture was stirred for 17 hours. To this solution was added sodium borohydride (110 mg, 2.91 mmol) in one portion and the mixture was stirred for 40 min. The reaction mixture was concentrated in vacuo and partitioned between CH2Cl2 (25 mL) and saturated aqueous sodium bicarbonate (25 mL). The aqueous layer was washed with CH2Cl2 (2×20 mL) and the combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo. The crude amine was dissolved in THF (10 mL) and protected with di-t-butyldicarbonate (1.0 g, 4.59 mmol). Purification of the crude material by column chromatography on silica gel (CH2Cl2/MeOH, 96:4 followed by 9:1) gave the desired product (110 mg, 22%) as a yellow oil.

出典