تفاعل #685023

معادلة التفاعل

benzyl 4-cyanopiperidine-1-carboxylate

2-chloroethyl chloromethyl ether

LiHMDS

→

title compound

المردود 86.2%

Benzyl 4-((2-chloroethoxy)methyl)-4-cyanopiperidine-1-carboxylate

المردود 86.2%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was quenched with water
2. 2
   غسيلthe organic phase was washed with brine
3. 3
   تجفيفdried (Na2SO4)
4. 4
   تركيزconcentrated
5. 5
   أخرىThe residue was purified by flash chromatography (1:1 EtOAc/hexane)

الإجراء التجريبي

A solution of benzyl 4-cyanopiperidine-1-carboxylate (10.0 g, 41 mmol) and 2-chloroethyl chloromethyl ether (6.3 mL, 49.2 mmol) in THF (80 mL) was cooled to −78° C. To this solution was added drop wise LiHMDS (50 mL, 50 mmol, 1N in THF) and the resulting mixture was gradually warmed to room temp over 5 h. The reaction was quenched with water and the organic phase was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (1:1 EtOAc/hexane) to give the title compound as yellow oil (11.9 g, 86% yield). 1H NMR (300 MHz, CDCl3) δ: 7.33-7.31 (5H, m), 5.10 (2H, d, J=5.9 Hz), 4.21 (2H, bs), 3.79-3.76 (2H, m), 3.63-3.60 (2H, m), 3.52-3.51 (2H, m), 3.09 (2H, bs), 1.96-1.92 (2H, m), 1.55-1.51 (2H, m).

المصدر