(1S,4R)-Methyl 4-((tert-butoxycarbonyl)amino)cyclopent-2-enecarboxylate

Name: (1S,4R)-Methyl 4-((tert-butoxycarbonyl)amino)cyclopent-2-enecarboxylate
Brand: ChemScene
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CAS No. 168683-02-1
Cat. No. CS-W006377
Purity≥98%
MDL No.MFCD02259716

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(1S,4R)-Methyl 4-((tert-butoxycarbonyl)amino)cyclopent-2-enecarboxylate|CS-W006377

Structure of 168683-02-1

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General Information

CAS No. 168683-02-1
Cat. No. CS-W006377
Purity ≥98%
MDL No. MFCD02259716
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₉NO₄
Molecular Weight 241.29
Synonym(s) None
SMILES O=C(N[C@H]1C=C[C@@H](C(OC)=O)C1)OC(C)(C)C

Description

This chiral cyclopentenecarboxylate features a protected amino group and a conjugated double bond, enabling direct incorporation into asymmetric synthesis workflows. The tert-butoxycarbonyl moiety provides stability and facilitates selective deprotection under mild acidic conditions.

Application

(1S,4R)-Methyl 4-((tert-butoxycarbonyl)amino)cyclopent-2-enecarboxylate serves as a stereochemically defined building block for the synthesis of bioactive cyclopentane derivatives. The enolizable ester and protected amine functionalities enable sequential transformations in medicinal chemistry workflows. Its bench-stable nature and compatibility with standard coupling and hydrogenation protocols facilitate efficient access to complex scaffolds.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  229613-83-6
- ~10%
- In-stock
  
  168683-02-1
References
- Kuraray Co., Ltd. Patent: EP1334969 A1, 2003 ;
Route2
- In-stock
  
  151792-53-9
- ~60%
- 168958-19-8
- In-stock
  
  168683-02-1
References
- DR. REDDY'S LABORATORIES LTD.; DR. REDDY'S LABORATORIES, INC.; LLOYD, Richard; PETERSON, Justine, Ann; JACKSON, Mark Patent: WO2011/3061 A2, 2011 ; Location in patent: Page/Page column 13-14 ;
Route3
- 79200-56-9
- ~%
- In-stock
  
  168683-02-1
References
- Chand; Montgomery; Kotian; Dehghani; El-Kattan; Lin; Hutchison; Babu; Bantia; Elliott Journal of Medicinal Chemistry, 2001 , vol. 44, # 25 p. 4379 - 4392

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

Quality Control

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Computational Chemistry Data

TPSA 64.63
LogP 1.6288
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Fatty ring compounds Cyclopentane compounds

Key Words

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(1S,4R)-Methyl 4-((tert-butoxycarbonyl)amino)cyclopent-2-enecarboxylate

CAS No. 168683-02-1

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Description

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Synthesis

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