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tert-Butyl ((1-(hydroxymethyl)cyclopropyl)methyl)carbamate

  • CAS No. 153248-46-5

  • Cat. No. CS-0044518
  • Purity≥97%
  • MDL No.MFCD09031543

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

tert-Butyl ((1-(hydroxymethyl)cyclopropyl)methyl)carbamate|CS-0044518

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General Information

  • CAS No. 153248-46-5
  • Cat. No. CS-0044518
  • Purity ≥97%
  • MDL No. MFCD09031543
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₉NO₃
  • Molecular Weight 201.26
  • Synonym(s) (1-Hydroxymethyl-cyclopropylmethyl); -carbamic acid tert-butyl ester
  • SMILES O=C(OC(C)(C)C)NCC1(CO)CC1

Description

tert-Butyl ((1-(hydroxymethyl)cyclopropyl)methyl)carbamate features a cyclopropylmethyl scaffold bearing a hydroxymethyl group and a tert-butoxycarbonyl-protected amine. This bifunctional building block enables direct incorporation of both polar and sterically constrained elements in synthetic sequences, offering enhanced solubility and stability under standard conditions.

Application

tert-Butyl ((1-(hydroxymethyl)cyclopropyl)methyl)carbamate serves as a stable, bench-friendly amino protecting group for cyclopropyl-containing amines. The carbamate functionality enables selective deprotection under mild acidic conditions, preserving the sensitive cyclopropyl ring and hydroxymethyl moiety. It facilitates efficient incorporation into diverse synthetic sequences, including peptide coupling and heterocycle construction, with excellent functional group tolerance and straightforward purification.

Synthesis

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    References

    • Buchholz, Mirko; Heiser, Ulrich; Schilling, Stephan; Niestroj, Andre J.; Zunkel, Katrin; Demuth, Hans-Ulrich Journal of Medicinal Chemistry, 2006 , vol. 49, # 2 p. 664 - 677
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    References

    • LEO Pharma A/S; NIELSEN, Simon Feldbaek; VIFIAN, Thomas; HORNEMAN, Anne Marie; LAU, Jesper Faergemann Patent: WO2010/69322 A1, 2010 ; Location in patent: Page/Page column 58 ;
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      tert-Butyl ((1-(hydroxymethyl)cyclopropyl)methyl)carbamate|CS-0044518
      153248-46-5

    References

    • Buchholz, Mirko; Heiser, Ulrich; Schilling, Stephan; Niestroj, Andre J.; Zunkel, Katrin; Demuth, Hans-Ulrich Journal of Medicinal Chemistry, 2006 , vol. 49, # 2 p. 664 - 677

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

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Computational Chemistry Data

  • TPSA   58.56
  • LogP   1.2836
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   3

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