tert-Butyl (2R)-2-(aminomethyl)morpholine-4-carboxylate

Name: tert-Butyl (2R)-2-(aminomethyl)morpholine-4-carboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 1174913-80-4
Cat. No. CS-M3423
Purity≥97%
MDL No.MFCD13189480

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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tert-Butyl (2R)-2-(aminomethyl)morpholine-4-carboxylate|CS-M3423

Structure of 1174913-80-4

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General Information

CAS No. 1174913-80-4
Cat. No. CS-M3423
Purity ≥97%
MDL No. MFCD13189480
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₂₀N₂O₃
Molecular Weight 216.28
Synonym(s) tert-Butyl-(2R)-2-(aminomethyl)morpholin-4-carboxylat
SMILES NC[C@H]1OCCN(C(OC(C)(C)C)=O)C1

Description

tert-Butyl (2R)-2-(aminomethyl)morpholine-4-carboxylate is a chiral, bench-stable building block featuring a morpholine ring with a protected aminomethyl side chain. This configuration enables selective incorporation into peptide backbones and bioactive scaffolds, particularly in medicinal chemistry campaigns requiring stereocontrolled synthesis. The tert-butyl ester group facilitates straightforward deprotection under mild acidic conditions, streamlining downstream functionalization.

Application

tert-Butyl (2R)-2-(aminomethyl)morpholine-4-carboxylate serves as a versatile chiral building block in medicinal chemistry, enabling the synthesis of morpholine-containing scaffolds via standard amine functionalization and deprotection protocols. Its tert-butyl ester group offers excellent bench stability and facilitates straightforward purification, while the pendant aminomethyl side chain provides a reactive handle for further diversification through alkylation, acylation, or conjugation reactions.

Synthesis

Route1
- 1308849-93-5
- ~75%
- In-stock
  
  1174913-80-4
References
- ASTRAZENECA AB; CANTIN, Louis-David; MARTINO, John; TOMASZEWSKI, Miroslaw; YU, Xiao Hong Patent: WO2012/158117 A1, 2012 ; Location in patent: Page/Page column 21; 23 ; WO 2012/158117 A1
Route2
- 1132683-15-8
- ~%
- In-stock
  
  1174913-80-4
References
- Journal of Medicinal Chemistry, , vol. 52, # 15 p. 4810 - 4819
Route3
- In-stock
  
  135065-76-8
- ~%
- In-stock
  
  1174913-80-4
References
- WO2011/62550 A1, ; WO 2011/062550 A1

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 64.79
LogP 0.581
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Morpholine compounds

Key Words

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tert-Butyl (2R)-2-(aminomethyl)morpholine-4-carboxylate

CAS No. 1174913-80-4

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