반응 #92591

반응 방정식

water

methyl azetidine-3-carboxylate

DIEA

bromomethyl benzene

→

product

수율 51.6%

Methyl 1-benzylazetidine-3-carboxylate

수율 51.6%

용매

DMF

반응 조건

후처리

1. 1
   추출extracted with EA (50 mL×3)
2. 2
   건조The combined organic layers were dried over Na2SO4
3. 3
   농축concentrated
4. 4
   기타purified by chromatography column on silica (EA/PE=1/4)

실험 절차

To a solution of methyl azetidine-3-carboxylate (5.0 g, 33.1 mmol) and DIEA (10.7 g, 82.8 mmol) in DMF (50 mL) was added dropwise bromomethyl benzene (5.7 g, 33.1 mmol) at 0° C. over 10 min. After stirring for 2 hr at rt, the mixture was poured to water (50 mL) and extracted with EA (50 mL×3). The combined organic layers were dried over Na2SO4 and concentrated and purified by chromatography column on silica (EA/PE=1/4) to give the product (3.5 g, 51.6%) as a light yellow oil. 1H NMR (DMSO-d6) δ 7.34-7.20 (m, 5H), 3.62 (s, 3H), 3.53 (s, 2H), 3.41-3.35 (m, 1H), 3.29-3.31 (m, 2H), 3.19-3.22 (m, 2H). MS (ESI, m/e) [M+1]+ 206.0.

출처