反応 #2267361

反応方程式

[1-cyclopropylmethyl-4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester

EtOH

3-cyanophenylboronic acid

Na2CO3

→

[4-(3′-cyano-biphenyl-4-yl)-1-cyclopropylmethyl-piperidin-4-ylmethyl]-carbamic acid isobutyl ester

収率 24.2%

溶媒

H2O

toluene

反応条件

後処理

1. 1
   その他partitioned between EtOAc (10 mL) and saturated Na2CO3 (10 mL)
2. 2
   洗浄The organic layer was washed with saturated Na2CO3 (3×10 mL) and saturated brine (2×10 mL)
3. 3
   乾燥dried over anhydrous sodium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他to give the crude product
7. 7
   その他This was purified by HPLC

実験手順

To a flask containing [1-cyclopropylmethyl-4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester (0.061 g, 0.13 mmol) was added Pd(PPh3)4 (0.015 g, 0.013 mmol, 10 mol %), 3-cyanophenylboronic acid (0.03 g, 0.2 mmol, 1.5 eq.) and Na2CO3 (0.212 g, 2 mmol). The mixture was suspended in toluene (3 mL), EtOH (1.5 mL) and H2O (1.0 mL) and heated to 80° C. for 18 h. The reaction mixture was cooled to room temperature and partitioned between EtOAc (10 mL) and saturated Na2CO3 (10 mL). The organic layer was washed with saturated Na2CO3 (3×10 mL) and saturated brine (2×10 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product. This was purified by HPLC to give the title compound [4-(3′-cyano-biphenyl-4-yl)-1-cyclopropylmethyl-piperidin-4-ylmethyl]-carbamic acid isobutyl ester as a brown solid (0.014 g, 24%). MS (ESI): 446.3/447.3 (M+1).

出典