(2R,4R)-tert-Butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Name: (2R,4R)-tert-Butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 141850-54-6
Cat. No. CS-0091642
Purity≥95%
MDL No.MFCD11617834

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(2R,4R)-tert-Butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate|CS-0091642

Structure of 141850-54-6

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General Information

CAS No. 141850-54-6
Cat. No. CS-0091642
Purity ≥95%
MDL No. MFCD11617834
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₉NO₄
Molecular Weight 217.26
Synonym(s) tert-Butyl (2R,4R)-4-hydroxy-2-(hydroxymethyl)-1-pyrrolidinecarboxylate
SMILES O=C(N1[C@@H](CO)C[C@@H](O)C1)OC(C)(C)C

Description

This chiral pyrrolidine derivative features a bench-stable tert-butyl ester and hydroxymethyl functionality, enabling direct incorporation into complex molecular architectures. The (2R,4R) stereochemistry ensures high diastereoselectivity in downstream transformations, while the protected alcohol groups offer orthogonal reactivity for selective derivatization under mild conditions.

Application

(2R,4R)-tert-Butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate serves as a versatile chiral building block in medicinal chemistry, enabling efficient access to pyrrolidine-containing scaffolds. The molecule features two orthogonal hydroxyl groups and a stable tert-butyl carbamate protecting group, facilitating selective derivatization and downstream functionalization. Its bench-stable nature and compatibility with standard coupling and reduction protocols make it ideal for multi-step synthesis of bioactive molecules.

Synthesis

Route1
- In-stock
  
  114676-69-6
- ~98%
- In-stock
  
  141850-54-6
References
- Jing, Qing; Li, Huiying; Roman, Linda J.; Martasek, Pavel; Poulos, Thomas L.; Silverman, Richard B. ACS Medicinal Chemistry Letters, 2014 , vol. 5, # 1 p. 56 - 60
Route2
- In-stock
  
  135042-12-5
- ~98%
- In-stock
  
  141850-54-6
References
- Fransson, Rebecca; McCracken, Alison N.; Chen, Bin; McMonigle, Ryan J.; Edinger, Aimee L.; Hanessian, Stephen ACS Medicinal Chemistry Letters, 2013 , vol. 4, # 10 p. 969 - 973
Route3
- 14044-65-6
- In-stock
  
  135042-12-5
- ~%
- In-stock
  
  141850-54-6
References
- Takeda Pharmaceutical Company Limited Patent: EP1553074 A1, 2005 ; Location in patent: Page/Page column 55 ;

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-H317
Precautionary Statements : P261-P264-P270-P272-P280-P302+P352-P330-P362+P364-P501

Quality Control

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Computational Chemistry Data

TPSA 70
LogP 0.349
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Alcohol

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

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(2R,4R)-tert-Butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

CAS No. 141850-54-6

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