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

  • CAS No. 92235-39-7

  • Cat. No. CS-B1207
  • Purity≥97%
  • MDL No.MFCD08166304

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

(S)-tert-Butyl (2-oxopiperidin-3-yl)carbamate|CS-B1207

Structure of 92235-39-7

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General Information

  • CAS No. 92235-39-7
  • Cat. No. CS-B1207
  • Purity ≥97%
  • MDL No. MFCD08166304
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₈N₂O₃
  • Molecular Weight 214.26
  • Synonym(s) (S)-3-(Boc-amino)-2-piperidone
  • SMILES O=C(OC(C)(C)C)N[C@@H]1C(NCCC1)=O

Description

(S)-tert-Butyl (2-oxopiperidin-3-yl)carbamate is a chiral building block featuring a protected piperidinone scaffold with defined stereochemistry at the 3-position. This bench-stable, moisture-tolerant reagent integrates seamlessly into peptide synthesis and medicinal chemistry workflows, enabling efficient access to bioactive nitrogen-containing heterocycles through straightforward deprotection and functionalization.

Application

(S)-tert-Butyl (2-oxopiperidin-3-yl)carbamate serves as a key chiral building block in the synthesis of piperidine-containing scaffolds, enabling efficient access to biologically relevant heterocycles. Its stable tert-butyl carbamate group offers excellent protection for primary amines, while the 2-oxo functionality facilitates downstream transformations such as reductive amination and ring expansion. The compound exhibits high bench stability, ease of purification, and compatibility with standard coupling and functionalization protocols, making it well-suited for medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • L-Ornithine (hydrochloride), 99%|CS-1268592
      3184-13-2
    • ~79%
    • In-stock
      (S)-tert-Butyl (2-oxopiperidin-3-yl)carbamate|CS-B1207
      92235-39-7

    References

    • ABBOTT LABORATORIES Patent: EP1428824 A1, 2004 ; Location in patent: Page 44 ;
  • Route2

    References

    • WO2004/22536 A1, ; Page 49-50 ; WO 2004/022536 A1
  • Route3

    References

    • Semple; Rowley; Brunck; Ha-Uong; Minami; Owens; Tamura; Goldman; Siev; Ardecky; Carpenter; Ge; Richard; Nolan; Hakanson; Tulinsky; Nutt; Ripka Journal of Medicinal Chemistry, 1996 , vol. 39, # 23 p. 4531 - 4536

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   67.43
  • LogP   0.7897
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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