ChemicalBook CAS DataBase List Pyrrolidine

Pyrrolidine synthesis

15synthesis methods

Product Name:Pyrrolidine
CAS Number:123-75-1
Molecular formula:C4H9N
Molecular Weight:71.12

Via overall 5-endo-trig cyclizations of homoallylic tosylamides.
Pyrrolidine can be produced from butanediol and ammonia, e.g., over an aluminum thorium oxide catalyst at 300°C or over a nickel catalyst at 200°C and 20 MPa under hydrogenation conditions. It can also be produced from THF and ammonia over aluminum oxide at 275-375°C.

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123-75-1
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Yield:123-75-1 94 %

Reaction Conditions:

with hydrogen;acetic acid in ethanol at 150; under 22502.3 Torr;

Steps:

2.3 Catalytic Performance Test

General procedure: 1 mmoL of the substrate and 0.015 g of the catalysts wereadded into a quartz reaction tube protected by high pressurevessel of stainless steel. Next, 10 mL of absolute ethanoland 0.5 mmoL of acid additive were mixed. The reactor waspurged three times with high purity hydrogen and then wascontinuously stirred for 18 h under 30 bar H2at 150 °C. Themixture was filtered and washed. Finally, the filtrate was collected.1 mL of concentrated hydrochloric acid was addedto form salt compounds and then 1 mmol of 1-(4-nitrophenyl)ethanone was thrown as internal standard. One tenthof the solution was taken out and concentrated to a solid.The obtained solid was dissolved in deuterium methanol toreceive 1H NMR of 2a and 2b in Table 2. Based on this,the yield can be determined. In order to obtain the isolatedpure target product, 0.25 g of Di-tert-butyl dicarbonate and0.06 g of 4-Dimethylaminopyridine were added into the filtratewhich was stirred for 2 h at ambient temperature. Bocprotectedproduct was purified by column chromatographyon silica gel using ethyl acetate and petroleum ether (1:10)as eluent and then confirmed by 1H NMR (400 MHz).

References:

Liu, Shuang;Zhao, Wei;Tang, Zhantong;Zhang, Li;Guo, Kailiang;Wang, Huishu;Men, Yong;Yang, Jun;Dai, Jun [Catalysis Letters,2022]

616-45-5 Synthesis