Benzyl (R)-2-cyanopyrrolidine-1-carboxylate

Name: Benzyl (R)-2-cyanopyrrolidine-1-carboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 620601-77-6
Cat. No. CS-0146417
Molecule weight230.26
Purity≥97%
MDL No.MFCD06796619

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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Benzyl (R)-2-cyanopyrrolidine-1-carboxylate|CS-0146417

Structure of 620601-77-6

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General Information

CAS No. 620601-77-6
Cat. No. CS-0146417
Purity ≥97%
MDL No. MFCD06796619
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₄N₂O₂
Molecular Weight 230.26
Synonym(s) (r)-1-Cbz-2-cyanopyrrolidine
SMILES N#C[C@@H]1N(C(OCC2=CC=CC=C2)=O)CCC1

Description

Benzyl (R)-2-cyanopyrrolidine-1-carboxylate is a chiral building block featuring a stereodefined pyrrolidine core with a nitrile group and benzyl ester. This configuration enables selective incorporation into bioactive molecules, particularly in the synthesis of pharmaceutical intermediates where stereocontrol is critical. The compound exhibits stability under standard handling conditions and facilitates efficient downstream transformations.

Application

Benzyl (R)-2-cyanopyrrolidine-1-carboxylate serves as a stereochemically defined building block for the synthesis of pyrrolidine-based scaffolds. The nitrile group enables subsequent transformations such as hydrolysis to carboxylic acids or reductive amination, while the benzyl ester offers convenient orthogonal protection and ease of removal under standard hydrogenolysis conditions. Its bench-stable nature and compatibility with diverse reaction conditions make it well-suited for medicinal chemistry campaigns requiring stereoselective heterocycle construction.

Synthesis

Route1
- 62937-47-7
- ~64%
- In-stock
  
  620601-77-6
References
- Cobb, Alexander J. A.; Shaw, David M.; Longbottom, Deborah A.; Gold, Johan B.; Ley, Steven V. Organic and Biomolecular Chemistry, 2005 , vol. 3, # 1 p. 84 - 96
Route2
- In-stock
  
  6404-31-5
- ~%
- In-stock
  
  620601-77-6
References
- Organic and Biomolecular Chemistry, , vol. 3, # 1 p. 84 - 96

Safety Information

Download SDS

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

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Computational Chemistry Data

TPSA 53.33
LogP 2.31118
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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Benzyl (R)-2-cyanopyrrolidine-1-carboxylate

CAS No. 620601-77-6

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