Methyl (2R)-1-(triphenylmethyl)aziridine-2-carboxylate

Name: Methyl (2R)-1-(triphenylmethyl)aziridine-2-carboxylate
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CAS No. 160233-42-1
Cat. No. CS-0049299
Purity≥97%
MDL No.None

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Methyl (2R)-1-(triphenylmethyl)aziridine-2-carboxylate|CS-0049299

Structure of 160233-42-1

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General Information

CAS No. 160233-42-1
Cat. No. CS-0049299
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₃H₂₁NO₂
Molecular Weight 343.42
Synonym(s) Methyl (R)-1-Trityl-2-aziridinecarboxylate
SMILES COC(=O)[C@H]1CN1C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1

Description

Methyl (2R)-1-(triphenylmethyl)aziridine-2-carboxylate is a chiral aziridine derivative featuring a sterically encumbered triphenylmethyl group that stabilizes the strained three-membered ring. This bench-stable, moisture-tolerant reagent enables direct functionalization of aziridines in asymmetric synthesis. The ester functionality facilitates downstream derivatization, while the (2R) stereochemistry ensures high diastereoselectivity in nucleophilic ring-opening reactions.

Application

Methyl (2R)-1-(triphenylmethyl)aziridine-2-carboxylate serves as a stable, bench-ready chiral building block for asymmetric synthesis. The triphenylmethyl (Trt) group provides robust protection of the aziridine nitrogen, enabling selective ring-opening reactions with nucleophiles under mild conditions. Its inherent chirality and functional group tolerance facilitate the construction of complex heterocyclic scaffolds and amino acid derivatives relevant to medicinal chemistry workflows.

Synthesis

Route1
- In-stock
  
  116457-91-1
- ~%
- In-stock
  
  160233-42-1
References
- Kato, Shiro; Harada, Hiroshi; Morie, Toshiya Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 21 p. 3219 - 3225
Route2
- 116457-92-2
- ~%
- In-stock
  
  160233-42-1
References
- Ki, Duk Park; Morieux, Pierre; Salome, Christophe; Cotten, Steven W.; Reamtong, Onrapak; Eyers, Claire; Gaskell, Simon J.; Stables, James P.; Liu, Rihe; Kohn, Harold Journal of Medicinal Chemistry, 2009 , vol. 52, # 21 p. 6897 - 6911
Route3
- 76-83-5
- ~%
- In-stock
  
  160233-42-1
References
- Kato, Shiro; Harada, Hiroshi; Morie, Toshiya Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 21 p. 3219 - 3225

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 29.31
LogP 3.8357
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 5

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Aziridine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Methyl (2R)-1-(triphenylmethyl)aziridine-2-carboxylate

CAS No. 160233-42-1

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