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(S)-tert-Butyl 2-methylaziridine-1-carboxylate

  • CAS No. 197020-60-3

  • Cat. No. CS-0079059
  • Purity≥98%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

(S)-tert-Butyl 2-methylaziridine-1-carboxylate|CS-0079059

Structure of 197020-60-3

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General Information

  • CAS No. 197020-60-3
  • Cat. No. CS-0079059
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₅NO₂
  • Molecular Weight 157.21
  • Synonym(s) tert-butyl (S)-2-methylaziridine-1-carboxylate
  • SMILES O=C(OC(C)(C)C)N1[C@@H](C)C1

Description

(S)-tert-Butyl 2-methylaziridine-1-carboxylate features a chiral aziridine core with a methyl group at the 2-position, enabling stereoselective transformations. The tert-butyl carbamate protecting group ensures stability and ease of handling under standard conditions. This bench-stable reagent integrates readily into asymmetric synthesis workflows, delivering controlled ring-opening reactions for complex nitrogen heterocycles.

Application

(S)-tert-Butyl 2-methylaziridine-1-carboxylate serves as a chiral building block for the synthesis of bioactive nitrogen-containing heterocycles. Its strained aziridine ring enables regioselective ring-opening reactions with nucleophiles, facilitating the installation of diverse functional groups under mild conditions. The tert-butyl carbamate group provides excellent stability and ease of removal during late-stage deprotection, enhancing its utility in medicinal chemistry workflows.

Synthesis

  • Route1

    References

    • Wessig, Pablo; Schwarz, Jutta Synlett, 1997 , vol. 1997, # 8 p. 893 - 894
  • Route2
    • (S)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate|CS-0338140
      126301-16-4
    • ~83%
    • In-stock
      (S)-tert-Butyl 2-methylaziridine-1-carboxylate|CS-0079059
      197020-60-3

    References

    • Adams, David; Benardeau, Agnes; Bickerdike, Mike J.; Bentley, Jon M.; Bissantz, Caterina; Bourson, Anne; Cliffe, Ian A.; Hebeisen, Paul; Kennett, Guy A.; Knight, Antony R.; Malcolm, Craig S.; Mizrahi, Jacques; Plancher, Jean-Marc; Richter, Hans; Roever, Stephan; Taylor, Sven; Vickers, Steven P. Chimia, 2004 , vol. 58, # 9 p. 613 - 620
  • Route3

    References

    • RANBAXY LABORATORIES LIMITED; DAS, Biswajit; UPADHYAY, Dilip, J.; PURNAPATRE, Kedar; GHOSH, Soma; KATOCH, Rita Patent: WO2012/14109 A1, 2012 ; WO 2012/014109 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02,GHS07
Signal Word : Danger
UN#: 1993
Class : 3
Packing Group : Ⅱ
Hazard Statements : H225-H315-H319
Precautionary Statements : P210-P233-P240-P241-P242-P243-P264-P280-P362+P364-P370+P378-P501

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Computational Chemistry Data

  • TPSA   29.31
  • LogP   1.6256
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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