반응 #1245504

반응 방정식

mono ethyl fumarate

trifluoroacetic acid

N-benzyl-N-(methoxymethyl)trimethylsilyl amine

→

title compound

(3S*,4S*)-1-Benzyl-pyrrolidine-3,4-dicarboxylic acid monoethyl ester

용매

methylene chloride

반응 조건

후처리

1. 1
   workup.WAITat RT over 48 h
2. 2
   농축The crude material is concentrated
3. 3
   기타purified by flash chromatography on silica gel (eluent: CH2Cl2/MeOH 85:15 to 85:15+2% NH4OH)

실험 절차

To a stirred solution of mono ethyl fumarate (2.85 g, 19.8 mmol) and trifluoroacetic acid (1.98 mmol, 0.15 mL) in methylene chloride (50 mL), N-benzyl-N-(methoxymethyl)trimethylsilyl amine (Aldrich) (9.41 g, 39.6 mmol) is added at 0° C. under N2. The mixture is stirred at 0° C. for 30 min and then at RT over 48 h. The crude material is concentrated and purified by flash chromatography on silica gel (eluent: CH2Cl2/MeOH 85:15 to 85:15+2% NH4OH) to give the title compound. MS (LC-MS): 278.0 [M+H]+. 1H-NMR (CD3OD, 400 MHz): δ=1.29 (t, 3H), 3.28 (m, 5H), 3.60 (m, 1 H), 4.07 (m, 2H), 4.20 (m, 2H), 7.47 (m, 5H) ppm.

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