反応 #438348

反応方程式

NaBH3CN

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

furfural

→

amine

収率 52.3%

N-(2-pyridinylmethyl)-N′-[2-furanylmethyl]-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

収率 52.3%

溶媒

methanol

反応条件

後処理

1. 1
   その他The solvent was removed under reduced pressure and CH2Cl2 (20 mL) and 1.0 M aqueous NaOH (10 mL)
2. 2
   workup.ADDITIONwere added to the residue
3. 3
   その他The phases were separated
4. 4
   抽出the aqueous phase was extracted with CH2Cl2 (3×10 mL)
5. 5
   乾燥The combined organic phases were dried (Na2SO4)
6. 6
   濃縮concentrated
7. 7
   その他Purification of the crude material by column chromatography silica gel (25:1 CH2Cl2-MeOH)

実験手順

To a stirred solution of N-(t-butyloxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.206 g, 0.449 mmol) in anhydrous methanol (10 mL), at room temperature, was added furfural (0.19 mL, 2.29 mmol) followed by NaBH3CN (0.070 g, 1.11 mmol) and the resultant solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and CH2Cl2 (20 mL) and 1.0 M aqueous NaOH (10 mL) were added to the residue. The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic phases were dried (Na2SO4) and concentrated. Purification of the crude material by column chromatography silica gel (25:1 CH2Cl2-MeOH) provided 0.103 g of the protected amine as a yellow oil.

出典