tert-Butyl N-[(1S,2S)-2-hydroxycyclopentyl]carbamate

Name: tert-Butyl N-[(1S,2S)-2-hydroxycyclopentyl]carbamate
Brand: ChemScene
Availability: InStock
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CAS No. 145106-43-0
Cat. No. CS-0039168
Purity≥97%
MDL No.MFCD11656038

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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tert-Butyl N-[(1S,2S)-2-hydroxycyclopentyl]carbamate|CS-0039168

Structure of 145106-43-0

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General Information

CAS No. 145106-43-0
Cat. No. CS-0039168
Purity ≥97%
MDL No. MFCD11656038
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₉NO₃
Molecular Weight 201.26
Synonym(s) (1S,2S)-trans-N-Boc-2-aminocyclopentanol
SMILES O=C(OC(C)(C)C)N[C@@H]1[C@@H](O)CCC1

Description

tert-Butyl N-[(1S,2S)-2-hydroxycyclopentyl]carbamate features a chiral cyclopentane scaffold with a hydroxyl group in the cis configuration, enabling stereocontrolled synthesis. The tert-butyloxycarbonyl (Boc) group provides robust protection for amine functionalities under acidic conditions. This bifunctional reagent integrates seamlessly into complex molecule assembly workflows, offering high stability and predictable reactivity in peptide and natural product synthesis.

Application

tert-Butyl N-[(1S,2S)-2-hydroxycyclopentyl]carbamate serves as a versatile chiral building block for asymmetric synthesis, enabling efficient construction of cyclopentane-based scaffolds. The protected amine and secondary alcohol functionalities exhibit excellent bench stability and compatibility with standard coupling and functionalization protocols. Its orthogonal reactivity facilitates sequential transformations in complex molecule assembly, particularly in medicinal chemistry and natural product synthesis.

Synthesis

Route1
- 445479-00-5
- ~99%
- In-stock
  
  145106-43-0
References
- BRISTOL-MYERS SQUIBB COMPANY Patent: WO2003/99276 A1, 2003 ; Location in patent: Page 267 ; WO 03/099276 A1
Route2
- 1430230-60-6
- ~88%
- In-stock
  
  145106-43-0
References
- ELI LILLY AND COMPANY; JADHAV, Prabhakar Kondaji; SAEED, Ashraf; GREEN, Jonathan Edward; KRISHNAN, Venkatesh; MATTHEWS, Donald Paul; STEPHENSON, Gregory Alan Patent: WO2013/55577 A1, 2013 ; Location in patent: Page/Page column 33 ;
Route3
- In-stock
  
  24424-99-5
- 125356-51-6
- ~71%
- In-stock
  
  145106-43-0
References
- Jin, Yonghao; Roycik, Mark D.; Bosco, Dale B.; Cao, Qiang; Constantino, Manuel H.; Schwartz, Martin A.; Sang, Qing-Xiang Amy Journal of Medicinal Chemistry, 2013 , vol. 56, # 11 p. 4357 - 4373

Safety Information

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GHS Pictogram :	GHS No : GHS07,GHS08,GHS09
Signal Word : Danger	UN#: 3077
Class : 9	Packing Group : Ⅲ
Hazard Statements : H302-H372-H400
Precautionary Statements : P260-P264-P273-P501

Quality Control

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Computational Chemistry Data

TPSA 58.56
LogP 1.4245
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Alcohol

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Fatty ring compounds Cyclopentane compounds

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tert-Butyl N-[(1S,2S)-2-hydroxycyclopentyl]carbamate

CAS No. 145106-43-0

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