(S)-tert-Butyl 3-(bromomethyl)piperidine-1-carboxylate

Name: (S)-tert-Butyl 3-(bromomethyl)piperidine-1-carboxylate
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CAS No. 158406-99-6
Cat. No. CS-M2743
Purity≥98%
MDL No.MFCD11111933

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Excepted Quantity	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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(S)-tert-Butyl 3-(bromomethyl)piperidine-1-carboxylate|CS-M2743

Structure of 158406-99-6

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General Information

CAS No. 158406-99-6
Cat. No. CS-M2743
Purity ≥98%
MDL No. MFCD11111933
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₂₀BrNO₂
Molecular Weight 278.19
Synonym(s) tert-butyl (3S)-3-(bromomethyl)piperidine-1-carboxylate
SMILES BrC[C@H]1CCCN(C(OC(C)(C)C)=O)C1

Description

(S)-tert-Butyl 3-(bromomethyl)piperidine-1-carboxylate features a chiral piperidine core with a bromomethyl handle, enabling stereoselective functionalization in medicinal chemistry. This bench-stable reagent integrates readily into synthesis workflows, delivering high-yielding couplings under mild conditions.

Application

(S)-tert-Butyl 3-(bromomethyl)piperidine-1-carboxylate serves as a versatile chiral building block for the synthesis of bioactive molecules, enabling efficient introduction of piperidine scaffolds with defined stereochemistry. The bromomethyl group facilitates nucleophilic substitution reactions, while the tert-butyl carbamate provides a stable, easily removable nitrogen protecting group. This reagent exhibits excellent bench stability and compatibility with standard coupling protocols, supporting scalable synthesis of pharmaceutical intermediates and functionalized heterocycles.

Synthesis

Route1
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  140695-84-7
- ~93%
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  158406-99-6
References
- Heerding, Dirk A.; Rhodes, Nelson; Leber, Jack D.; Clark, Tammy J.; Keenan, Richard M.; Lafrance, Louis V.; Li, Mei; Safonov, Igor G.; Takata, Dennis T.; Venslavsky, Joseph W.; Yamashita, Dennis S.; Choudhry, Anthony E.; Copeland, Robert A.; Lai, Zhihong; Schaber, Michael D.; Tummino, Peter J.; Strum, Susan L.; Wood, Edgar R.; Duckett, Derek R.; Eberwein, Derek; Knick, Victoria B.; Lansing, Timothy J.; McConnell, Randy T.; Zhang, ShuYun; Minthorn, Elisabeth A.; Concha, Nestor O.; Warren, Gregory L.; Kumar, Rakesh Journal of Medicinal Chemistry, 2008 , vol. 51, # 18 p. 5663 - 5679

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 29.54
LogP 3.0284
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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(S)-tert-Butyl 3-(bromomethyl)piperidine-1-carboxylate

CAS No. 158406-99-6

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