2-PYRROLIDIN-1-YLMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID BENZYL ESTER synthesis
- Product Name:2-PYRROLIDIN-1-YLMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID BENZYL ESTER
- CAS Number:134591-58-5
- Molecular formula:C17H24N2O2
- Molecular Weight:288.38
51207-66-0
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Yield:134591-58-5 87%
Reaction Conditions:
with potassium carbonate in acetonitrile at 20;Inert atmosphere;
Steps:
2.1 2.2.1 Benzyl (S)-2-[(pyrrolidin-1-yl)methyl]pyrrolidine-1-carboxylate 2
Benzyl chloroformate (0.39 g, 2.3 mmol) was added dropwise to a suspension of (S)-1-[(pyrrolidin-2-yl)methyl]pyrrolidine 1 (0.25 g, 1.6 mmol) and K2CO3 (0.46 g, 3.3 mmol) in anhydrous CH3CN at 0 °C under argon. After stirring overnight at room temperature the reaction mixture was diluted with H2Odest and repeatedly extracted with diethyl ether. The combined organic layers were washed once with brine, dried over Na2SO4 and the solvent was removed under reduced pressure.
The crude product was purified via chromatography (CH2Cl2/MeOH) to obtain benzyl (S)-2-[(pyrrolidin-1-yl)methyl]pyrrolidine-1-carboxylate 2 as light yellow oil. Yield: 0.42 g, 87%. Rf = 0.7 (CH2Cl2/MeOH 4:1). [α]58920 = + 51.5 (EtOH, c = 1.03).
1H NMR (400 MHz, CDCl3): δ = 1.69-2.00 (m, 8H), 2.41-2.62 (m, 6H), 3.40 (s, 2H), 3.96 (br s, 1H), 5.08-5.17 (m, 2H), 7.29-7.34 (m, 5H). 13C NMR (100 MHz, CDCl3): δ = 23.5, 29.3, 46.5, 54.6, 56.7, 59.1, 66.6, 127.9, 137.0, 155.0. ATR-IR: λ = 2961, 2881, 2789, 1699, 1410, 1358, 1104, 698 cm-1. HR-MS: m/z (calculated) = 288.1838, m/z (found) = 289.1911 (M++H).
References:
Vasiloiu, Maria;Rainer, Daniel;Gaertner, Peter;Reichel, Christian;Schr?der, Christian;Bica, Katharina [Catalysis Today,2013,vol. 200,# 1,p. 80 - 86]
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