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trans-tert-Butyl (4-hydroxycyclohexyl)carbamate

  • CAS No. 111300-06-2

  • Cat. No. CS-W003130
  • Purity≥97%
  • MDL No.MFCD03844613

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

trans-tert-Butyl (4-hydroxycyclohexyl)carbamate|CS-W003130

Structure of 111300-06-2

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General Information

  • CAS No. 111300-06-2
  • Cat. No. CS-W003130
  • Purity ≥97%
  • MDL No. MFCD03844613
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₂₁NO₃
  • Molecular Weight 215.29
  • Synonym(s) Trans-T-Butyl-4-Hydroxycyclohexylcarbamate
  • SMILES O=C(OC(C)(C)C)N[C@@H]1CC[C@H](CC1)O

Description

trans-tert-Butyl (4-hydroxycyclohexyl)carbamate is a bench-stable, moisture-tolerant protecting group for primary alcohols, featuring a rigid cyclohexyl scaffold that enables stereoselective functionalization. The para-hydroxy substituent enhances solubility in organic media while the tert-butyl carbamate moiety facilitates clean deprotection under mild acidic conditions. This compound serves as a key intermediate in the synthesis of complex polyol architectures and bioactive molecules requiring controlled hydroxyl handling.

Application

trans-tert-Butyl (4-hydroxycyclohexyl)carbamate serves as a stable, bench-friendly protecting group for primary amines in complex molecule synthesis. Its trans-configured cyclohexyl scaffold provides predictable stereochemistry and facilitates selective deprotection under mild acidic conditions. The pendant hydroxyl group enables orthogonal functionalization or further derivatization, making it particularly valuable in the construction of chiral heterocycles and bioactive scaffolds.

Synthesis

  • Route1

    References

    • Carter, Percy H.; Cherney, Robert J.; Batt, Douglas G.; Brown, Gregory D.; Duncia, John V.; Gardner, Daniel S.; Yang, Michael G. Patent: US2005/54626 A1, 2005 ; Location in patent: Page/Page column 47 ; US 20050054626 A1
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    References

    • Almirall, S.A.; Prat Quinones, Maria; Fonquerna Pou, Silvia; Puig Duran, Carlos; Lumeras Amador, Wenceslao; Aiguade Bosch, Jose; Caturla Javaloyes, Juan Francisco Patent: EP2386555 A1, 2011 ; Location in patent: Paragraph 0073 ;
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    References

    • Raju; Anandan, Sampathkumar; Gu, Shihai; Herradura, Prudencio; O'Dowd, Hardwin; Kim, Bum; Gomez, Marcela; Hackbarth, Corinne; Wu, Charlotte; Wang, Wen; Yuan, Zhengyu; White, Richard; Trias, Joaquim; Patel, Dinesh V. Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 12 p. 3103 - 3107

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   1.8146
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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