反応 #312570

反応方程式

3-(2-Benzyl-2-aza-bicyclo[3.3.1]non-5-yl)-phenylamine

2-methoxy-ethanesulfonyl chloride

→

2-Methoxy-ethanesulfonic acid [3-(2-benzyl-2-aza-bicyclo[3.3.1]non-5-yl)-phenyl]-amide

溶媒

toluene

pyridine

反応条件

後処理

1. 1
   濃縮concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2
3. 3
   洗浄washed with saturated aqueous NaHCO3 solution (100 mL)
4. 4
   抽出The aqueous layer was extracted with CH2Cl2 (2×50 ml)
5. 5
   濃縮the organic layer was concentrated to an oil
6. 6
   workup.DISSOLUTIONThis was dissolved in EtOAc which
7. 7
   その他to separate
8. 8
   その他The EtOAc layer was separated
9. 9
   洗浄washed with saturated aqueous NaHCO3 solution (100 mL)
10. 10
    抽出The aqueous layer was extracted with EtOAc (2×50 ml)
11. 11
    洗浄the combined organic layer was washed with saturated aqueous NaCl solution (50 ml)
12. 12
    乾燥dried over Na2SO4
13. 13
    ろ過filtered
14. 14
    濃縮concentrated to a crude orange liquid (3.77 g, ˜100%)

実験手順

3-(2-Benzyl-2-aza-bicyclo[3.3.1]non-5-yl)-phenylamine (2.71 g, 8.84 mmol) stirred in pyridine (25 ml) at 0° C. was charged with 2-methoxy-ethanesulfonyl chloride (2.1 g, 13.26 mmol) dropwise causing a color change from yellow to bright orange. The reaction was allowed to warm to room temperature gradually and stirred 18 h. The reaction mixture was diluted with toluene and concentrated in vacuo. The residue was dissolved in CH2Cl2 and washed with saturated aqueous NaHCO3 solution (100 mL). The aqueous layer was extracted with CH2Cl2 (2×50 ml) and the organic layer was concentrated to an oil. This was dissolved in EtOAc which caused an oil to separate. The EtOAc layer was separated and washed with saturated aqueous NaHCO3 solution (100 mL). The aqueous layer was extracted with EtOAc (2×50 ml) and the combined organic layer was washed with saturated aqueous NaCl solution (50 ml), dried over Na2SO4, filtered and concentrated to a crude orange liquid (3.77 g, ˜100%). (TLC 75% EtOAc/hexanes Rf 0.48);

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