34951-59-2

Usage

Ethyl ester derivative

1H-Pyrrolizine-7-carboxylic acid, 2,3-dihydro-, ethyl ester is an ethyl ester derivative of 1H-Pyrrolizine-7-carboxylic acid, meaning it has an ethoxycarbonyl group (-COOEt) attached to the molecule.

Heterocyclic compound

1H-Pyrrolizine-7-carboxylic acid, 2,3-dihydro-, ethyl ester contains a pyrrolizine ring system, which is a five-membered heterocyclic ring containing one or more heteroatoms (in this case, nitrogen).

Potential applications

1H-Pyrrolizine-7-carboxylic acid, 2,3-dihydro-, ethyl ester may be used as an intermediate in the synthesis of pharmaceuticals or other organic compounds, and has potential applications in medicinal chemistry and drug development.

Variable properties and uses

The exact properties and uses of 1H-Pyrrolizine-7-carboxylic acid, 2,3-dihydro-, ethyl ester may vary depending on the specific context in which it is being utilized, such as the desired chemical reaction or the target application in drug development.

Upstream product

• 41646-10-0 2,3,5,6-Tetrahydro-1H-pyrrolizin-7-carbonsaeure-ethylester 
• 67-68-5 dimethyl sulfoxide 
• 156237-71-7 Ethyl 1-(3-iodopropyl)pyrrole-3-carboxylate 
• 108139-96-4 α-(Tetrahydropyrrolylidene-2) acetate d'ethyle 
• 37964-17-3 pyrrole-3-carboxylic acid ethyl ester 
• 156237-57-9 Ethyl 1-(3-chloropropyl)pyrrole-3-carboxylate 
• 99125-87-8 (Z)-6-Hydroxy-2-vinyl-hex-2-enoic acid ethyl ester 
• 99125-92-5 (Z)-6-(tert-Butyl-dimethyl-silanyloxy)-2-vinyl-hex-2-enoic acid ethyl ester 
• 128845-77-2 (Z)-6-Methanesulfonyloxy-2-vinyl-hex-2-enoic acid ethyl ester 
• 99125-91-4 6-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-vinyl-hexanoic acid ethyl ester 

Downstream Products

• 27628-47-3 Dehydrosupinidin 
• 116515-48-1 1,2-dihydro-3H-pyrrolizine-7-carboxylic acid 
• 27628-46-2 Danaidal 

Relevant academic research and scientific papers

Synthesis of fused pyrrolines by the intramolecular cycloaddition of azides. Application to the pyrrolizidine alkaloids

Intramolecular 1,3-dipolar cycloaddition of an azide proceeds through triazoline and vinyl aziridine, resulting in the formation of a 1,5-homodienyl shift product and two tetrahydropyrrolizines, one of which represents a formal total synthesis of supinidine.

Synthesis of 2,3-dihydropyrrolizines from Weinreb 3-(pyrrolidin-2-ylidene)propionamides or Weinreb N-vinylprolinamides

Weinreb 3-(pyrrolidin-2-ylidene)propionamides and Weinreb N-vinylprolinamides were used for the synthesis of 2,3-dihydropyrrolizines. The selective reaction of the carboxamide group with organometallic compounds allowed us to obtain a great variety of carbonyl intermediates, analogous to the Hantzsch and Knorr pyrrole synthesis, which were thermally cyclized.

Oxidative radical cyclization of (ω-iodoalkyl)indoles and pyrroles. Synthesis of (-)-monomorine and three diastereomers

Addition of excess hydrogen peroxide (10 equiv) to a sonicated solution of FeSO4:7H2O (1 equiv) in DMSO containing the N-(ω-iodoalkyl)indoles 4, 5, 11, and 13 effected oxidative radical cyclization to 6, 7, 14, and 15, respectively. The (ω-iodoalkyl)pyrroles 21, 22, 27, 38, and 49 underwent analogous cyclization reactions to 23, 24, 28, 39, and 50, respectively. The regiochemistry of these radical cyclization reactions was correctly predicted by FMO calculations in all cases but one. For compound 38, FMO calculations indicated that radical attack should take place at both C-3 and C-5. Only the product of cyclization at C-5, i.e., 39, was observed. The enantiomerically pure bicyclic ketone 42, prepared by the above technique from the iodide 53, was converted into 55 which, on catalytic reduction (H2/Rh-Al2O3), gave a mixture of (-)-monomorine (40) and three of its diastereomers 56-58.

Synthesis of 2,3-Dihydro-1H-pyrrolizine-7-carbaldehyde, the Sex Pheromone Danaidal

Danaidal (4) can easily be obtained in high yields from ethyl 2,3,5,6-tetrahydro-1H-pyrrolizine-7-carboxylate (1) via sulphur dehydrogenation or MnO2 oxidation, subsequent reduction to dehydrosupinidine (3), and further oxidation to the desired title compound 4.