反応 #2267358

反応方程式

pyridine

4-aminomethyl-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

isobutyl chloroformate

→

4-(4-iodo-phenyl)-4-(isobutoxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester

収率 62.5%

溶媒

EtOAc

CH2Cl2

反応条件

後処理

1. 1
   洗浄washed with saturated aqueous NaHCO3 (5 mL) and saturated brine (5 mL)
2. 2
   乾燥dried over Na2SO4
3. 3
   ろ過Filtration and rotary evaporation

実験手順

To a stirred solution of 4-aminomethyl-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.10 g, 0.24 mmol) in CH2Cl2 (1.0 mL) at room temperature under Ar was added isobutyl chloroformate(0.033 mL, 0.26 mmol, 1.1 eq.) followed by pyridine (0.25 mL). The mixture was stirred at room temperature for 16 h, diluted with EtOAc (5 mL), washed with saturated aqueous NaHCO3 (5 mL) and saturated brine (5 mL) and dried over Na2SO4. Filtration and rotary evaporation gave the crude 4-(4-iodo-phenyl)-4-(isobutoxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester as a yellow oil (0.075 g, 0.15 mmol, ˜62%). 1H NMR (300 MHz, CDCl3): δ 7.81 (d, 2H), 7.15 (d, 2H), 4.42 (br.t, 1H), 3.88 (d, 2H), 3.79 (m, 2H), 3.42 (br.m, 2H), 3.25 (br.t, 2H), 2.13 (br.m, 3H), 1.88 (m, 3H), 1.54 (s, 9H), 0.99 (d, 6H). MS: 417 (M−Boc).

出典