反応 #2267360

反応方程式

Na(OAc)3BH

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

cyclopropanecarboxaldehyde

HOAc

→

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

収率 95.0%

溶媒

EtOAc

ClCH2CH2Cl

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred for 16 h
2. 2
   洗浄washed with saturated aqueous NaHCO3 solution (10 mL) and saturated brine (10 mL)
3. 3
   乾燥The combined organic layers were dried over Na2SO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated by rotary evaporation

実験手順

To a stirred solution of [4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester (0.058 g, 0.14 mmol) in ClCH2CH2Cl (0.75 mL) at room temperature under Ar was added cyclopropanecarboxaldehyde (0.012 mL, 0.156 mmol, 1.2 eq.) and HOAc (0.075 mL, 1% v/v). The mixture was stirred for 0.5 h then Na(OAc)3BH (0.041 g, 0.2 mmol, 1.5 eq.) was added. The mixture was stirred for 16 h, diluted with EtOAc (10 mL) and washed with saturated aqueous NaHCO3 solution (10 mL) and saturated brine (10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated by rotary evaporation to give [1-cyclopropylmethyl-4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester (0.061 g, 95%). MS (ESI): 471.2/472.2 (M+1).

出典