tert-Butyl (S)-(2-oxopyrrolidin-3-yl)carbamate

Name: tert-Butyl (S)-(2-oxopyrrolidin-3-yl)carbamate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 92235-34-2
Cat. No. CS-W007134
Purity≥95%
MDL No.MFCD03426144

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Type	HazMat Fee
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FedEx Limited Quantities Ground	$0.00
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tert-Butyl (S)-(2-oxopyrrolidin-3-yl)carbamate|CS-W007134

Structure of 92235-34-2

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General Information

CAS No. 92235-34-2
Cat. No. CS-W007134
Purity ≥95%
MDL No. MFCD03426144
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₆N₂O₃
Molecular Weight None
Synonym(s) (S)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamate
SMILES O=C(OC(C)(C)C)N[C@@H]1C(NCC1)=O

Description

tert-Butyl (S)-(2-oxopyrrolidin-3-yl)carbamate serves as a chiral building block for synthesizing pyrrolidine-based pharmaceuticals. This bench-stable, moisture-tolerant reagent features a protected (S)-configured pyrrolidin-3-one moiety, enabling direct incorporation into complex heterocycles via standard coupling protocols without racemization.

Application

tert-Butyl (S)-(2-oxopyrrolidin-3-yl)carbamate serves as a chiral building block for the synthesis of pyrrolidine-based scaffolds, enabling efficient access to bioactive heterocycles. Its stable tert-butyl carbamate group facilitates straightforward protection and deprotection under mild acidic conditions, while the (S)-configured oxopyrrolidinyl moiety supports stereoselective transformations. The compound exhibits excellent functional group tolerance and is well-suited for iterative synthesis in medicinal chemistry workflows.

Synthesis

Route1
- In-stock
  
  24424-99-5
- 4128-00-1
- ~80%
- In-stock
  
  92235-34-2
References
- Xcovery, Inc. Patent: US2009/76005 A1, 2009 ; Location in patent: Page/Page column 29; 30 ; US 20090076005 A1
Route2
- 762-75-4
- 4128-00-1
- ~70%
- In-stock
  
  92235-34-2
References
- VERTEX PHARMACEUTICALS INCORPORATED; GREEN, Jeremy; WILSON, Dean, M.; KONG, Laval, Chan Chun; DAS, Sanjoy, Kumar; POISSON, Carl; COURT, John, J.; TANG, Qing; LI, Pan; COLLIER, Philip, N.; WAAL, Nathan; LAUFFER, David, J.; DORSCH, Warren Patent: WO2012/6055 A2, 2012 ; Location in patent: Page/Page column 158 ; WO 2012/006055 A2
Route3
- In-stock
  
  24424-99-5
- 118507-50-9
- ~73%
- In-stock
  
  92235-34-2
References
- Tang, Tian; Zhu, Chen; Huang, Pei-Qiang Heterocycles, 2004 , vol. 64, p. 121 - 128

Safety Information

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Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

Quality Control

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Computational Chemistry Data

TPSA 67.43
LogP 0.3996
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Key Words

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tert-Butyl (S)-(2-oxopyrrolidin-3-yl)carbamate

CAS No. 92235-34-2

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