tert-Butyl N-[(1S,2S)-2-aminocyclohexyl]carbamate

Name: tert-Butyl N-[(1S,2S)-2-aminocyclohexyl]carbamate
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CAS No. 180683-64-1
Cat. No. CS-0000127
Molecule weight214.30
Purity≥96%
MDL No.MFCD08460986

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Excepted Quantity	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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tert-Butyl N-[(1S,2S)-2-aminocyclohexyl]carbamate|CS-0000127

Structure of 180683-64-1

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General Information

CAS No. 180683-64-1
Cat. No. CS-0000127
Purity ≥96%
MDL No. MFCD08460986
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₂₂N₂O₂
Molecular Weight 214.30
Synonym(s) None
SMILES O=C(OC(C)(C)C)N[C@@H](CCCC1)[C@H]1N

Description

tert-Butyl N-[(1S,2S)-2-aminocyclohexyl]carbamate is a stereochemically defined chiral auxiliary featuring a protected primary amine on a rigid cyclohexyl scaffold. This bench-stable derivative facilitates asymmetric synthesis and peptide coupling workflows, enabling controlled functionalization in complex molecule assembly.

Application

tert-Butyl N-[(1S,2S)-2-aminocyclohexyl]carbamate serves as a versatile chiral building block for medicinal chemistry and catalytic asymmetric synthesis. The (1S,2S)-configured cyclohexylamine moiety provides a rigid, stereodefined scaffold that facilitates enantioselective transformations. The tert-butyl carbamate group offers excellent bench stability and can be selectively removed under mild acidic conditions, enabling straightforward access to the free amine. This compound functions effectively in peptide coupling, metal-catalyzed C–H functionalization, and heterocycle construction, with high compatibility across diverse reaction conditions.

Synthesis

Route1
- In-stock
  
  24424-99-5
- 21436-03-3
- ~85%
- In-stock
  
  180683-64-1
References
- Garimella, Praveena D.; Datta, Ankona; Romanini, Dante W.; Raymond, Kenneth N.; Francis, Matthew B. Journal of the American Chemical Society, 2011 , vol. 133, # 37 p. 14704 - 14709
Route2
- 880644-81-5
- ~%
- In-stock
  
  180683-64-1
References
- WO2006/33714 A2, ; Page/Page column 24-25 ;
Route3
- In-stock
  
  24424-99-5
- ~%
- In-stock
  
  180683-64-1
References
- US2003/22831 A1, ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05
Signal Word : Danger	UN#: 3259
Class : 8	Packing Group : Ⅲ
Hazard Statements : H314
Precautionary Statements : P260-P264-P280-P301+P330+P331-P304+P340-P363-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 64.35
LogP 1.781
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Bioactive Molecules Dye and Bio-assay Reagents

Building Blocks Functional Group Boc

Building Blocks Functional Group Amine

Building Blocks Skeleton Fatty ring compounds Cyclohexane compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Catalysts and Ligands Ligands Diamine Ligands DACH & Trost Ligands

Catalysis Asymmetric Synthesis Chiral Catalysts, Chiral Ligands, Chiral Reagents Epoxidation

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tert-Butyl N-[(1S,2S)-2-aminocyclohexyl]carbamate

CAS No. 180683-64-1

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