(S)-1-tert-Butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate

Name: (S)-1-tert-Butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 84348-39-0
Cat. No. CS-0009248
Purity≥97%
MDL No.MFCD15832853

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FedEx Limited Quantities Ground	$0.00
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(S)-1-tert-Butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate|CS-0009248

Structure of 84348-39-0

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General Information

CAS No. 84348-39-0
Cat. No. CS-0009248
Purity ≥97%
MDL No. MFCD15832853
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₉NO₄
Molecular Weight 241.28
Synonym(s) N-Boc-4-methylene-L-proline Methyl Ester
SMILES O=C([C@H](C1)N(C(OC(C)(C)C)=O)CC1=C)OC

Description

This chiral pyrrolidine derivative features a tert-butyl ester and methylenepyrrolidine scaffold, offering high stereochemical integrity and stability under standard conditions. The electron-rich alkene moiety enables efficient coupling reactions, while the sterically protected tertiary carbon enhances resistance to racemization. Ideal for asymmetric synthesis and medicinal chemistry applications requiring robust, bench-stable building blocks.

Application

(S)-1-tert-Butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate serves as a chiral building block for the synthesis of pyrrolidine-based heterocycles, enabling stereoselective functionalization at the C4 methylene position. Its bench-stable nature and orthogonal protecting groups facilitate downstream transformations in medicinal chemistry workflows. The molecule functions as a versatile scaffold for constructing biologically relevant frameworks through standard coupling and reduction protocols.

Synthesis

Route1
- In-stock
  
  24424-99-5
- ~%
- In-stock
  
  84348-39-0
- 256488-01-4
References
- Tymtsunik, Andriy V.; Bilenko, Vitaliy A.; Ivon, Yevhen M.; Grygorenko, Oleksandr O.; Komarov, Igor V. Tetrahedron Letters, 2012 , vol. 53, # 30 p. 3847 - 3849
Route2
- In-stock
  
  40216-83-9
- ~%
- In-stock
  
  84348-39-0
- 256488-01-4
References
- Tymtsunik, Andriy V.; Bilenko, Vitaliy A.; Ivon, Yevhen M.; Grygorenko, Oleksandr O.; Komarov, Igor V. Tetrahedron Letters, 2012 , vol. 53, # 30 p. 3847 - 3849
Route3
- In-stock
  
  102195-80-2
- 19493-09-5
- ~%
- In-stock
  
  84348-39-0
- 256488-01-4
References
- Tymtsunik, Andriy V.; Bilenko, Vitaliy A.; Ivon, Yevhen M.; Grygorenko, Oleksandr O.; Komarov, Igor V. Tetrahedron Letters, 2012 , vol. 53, # 30 p. 3847 - 3849

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 55.84
LogP 1.725
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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(S)-1-tert-Butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate

CAS No. 84348-39-0

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